2-Oxo-2-phenylacetic acid (Phenylglyoxylic Acid) by Asch

Reactions (3319)

Yield

Substances (4702)

Citations (815)

Conditions

References

100

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Rx-ID: 43375578

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55%

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Stage #1: With palladium(II) trifluoroacetate; sodium acetate; silver carbonate in DME

T=150°C; 28 h; Sealed tube; Stage #2: With copper(II) oxide in DME; N,N-dimethyl-formamide

T=150°C; 28 h; Sealed tube; Concentration; Hide Experimental Procedure

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Shaanxi Normal University; Shi, Xianying; Sun, Man; Fan, Juan; Wei, Junfa

Patent: CN105418393 A, 2016 ; Location in patent: Paragraph 0013; 0014; 0015; 0016; 0017 ; Title/Abstract Full Text Show Details

Was added 0.0136g (0.1mmol) p-toluic acid, 0.0450g (0.3mmol) of benzoyl formic acid in 10mL pressure reaction tube, 0.0033g (0.01mmol) palladium trifluoroacetate, 0.0689g (0.25mmol) silver carbonate , 0.0164g (0.2mmol) of anhydrous sodium acetate, ImL ethylene glycol dimethyl ether, the reaction mixture was stirred under a sealed condition 150 deg.] C 28 hours, cooled to room temperature after completion of the reaction, was added 0.0159g (0.2mmol) CuO, 0.2mL N, N- dimethylformamide, stirred under confined conditions 150 28 hours the reaction, by column chromatography on silica gel catalyst was removed by filtration and the salts, by thin layer chromatography to give 3-methyl benzophenone, which The yield was 55percent, and structural characterization data are as follows:

101

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Rx-ID: 43606896

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60%

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With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide in ethyl acetate

T=80°C; 24 h; Sealed tube; Hide Experimental Procedure

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Chang, Li-Ming; Yuan, Gao-Qing

Tetrahedron, 2016 , vol. 72, # 44 p. 7003 - 7007 Title/Abstract Full Text Show Details

14:A typical procedure for the synthesis of α-acyloxycarbonyl compounds

General procedure: The mixture of phenylglyoxylic acid (0.2mmol), propiophenone (0.2mmol), TBHP (0.4mmol), TBAI (0.04mmol) and ethyl acetate (2mL) was stirred at 80°C for 24h in a 15mL sealed tube successively. After cooling down, the reaction mixture was washed with Na2S2O3 solution, and extracted by ethyl acetate for three times. The obtained top organic layer was dried with anhydrous MgSO4. After drying, the mixture was concentrated under vacuum, and the crude product was purified by column chromatography on silica gel with petroleum ether–ethyl acetate (50:1) as eluent.

102

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Rx-ID: 43606912

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57%

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With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide in ethyl acetate

T=80°C; 24 h; Sealed tube; Hide Experimental Procedure

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Chang, Li-Ming; Yuan, Gao-Qing

Tetrahedron, 2016 , vol. 72, # 44 p. 7003 - 7007 Title/Abstract Full Text Show Details

18:A typical procedure for the synthesis of α-acyloxycarbonyl compounds

103

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Rx-ID: 43606925

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63%

With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide in ethyl acetate

T=80°C; 24 h; Sealed tube; Hide Experimental Procedure

Chang, Li-Ming; Yuan, Gao-Qing

Tetrahedron, 2016 , vol. 72, # 44 p. 7003 - 7007 Title/Abstract Full Text Show Details

20:A typical procedure for the synthesis of α-acyloxycarbonyl compounds

104

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Rx-ID: 43757140

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62%

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With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride in dichloromethane

T=0°C; 24 h; Hide Experimental Procedure

Seufert, Florian; Kuhn, Maximilian; Hein, Michael; Weiwad, Matthias; Vivoli, Mirella; Norville, Isobel H.; Sarkar-Tyson, Mitali; Marshall, Laura E.; Schweimer, Kristian; Bruhn, Heike; Rösch, Paul; Harmer, Nicholas J.; Sotriffer, Christoph A.; Holzgrabe, Ulrike Bioorganic and Medicinal Chemistry, 2016 , vol. 24, # 21 p. 5134 - 5147 Title/Abstract Full Text Show Details

(S)-3-(Pyridin-3-yl)propyl 1-(2-oxo-2-phenylacetyl)piperidine-2-carboxylate (S-5l)

For the synthesis of S-5l an amidation with 8a (1equiv) and phenylglyoxalic acid (1.0equiv) in 20mL anhydrous CH2Cl2 was performed at 0°C using EDC·HCl (1.3equiv) and HOBt (0.5equiv). The mixture was stirred until completion (TLC control) and after purification by means of flash-chromatography the compound was obtained as a yellow oil (0.20g, 62percent). The 1H NMR showed the presence of a 77–23 mixture of rotamers. Rotamer a: 1H NMR (400MHz, CDCl3) δ 8.40–8.50 (m, 2H), 8.01–8.05 (m, 2H), 7.58–7.67 (m, 1H), 7.43–7.55 (m, 3H),

7.19–7.25 (m, 1H), 5.42 (d, 1H, J=5.2Hz), 4.26 (t, 2H, J=6.4Hz), 3.48–3.55 (m, 1H), 3.26 (ddd, 1H, J=13.0, 13.1, 3.0Hz), 2.75 (t, 2H, J=7.8Hz), 2.01–2.10 (m, 2H), 1.31–1.94 (m, 6H); 13C NMR (100MHz, CDCl3) δ 191.6, 170.4, 167.4, 149.9, 147.8, 136.1, 135.9, 134.8,

133.2, 129.7 (2C), 129.1 (2C), 123.4, 64.6, 51.6, 44.3, 30.0, 29.3, 26.4, 24.9, 21.2. Rotamer b (only different signals to a are shown): 1H NMR (400MHz, CDCl3) δ 7.96–7.99 (m, 2H), 4.61–4.68 (m, 1H), 4.39 (d, 1H, J=4.9), 3.03 (ddd, 1H, J=13.3, 13.3, 3.0Hz), 2.61 (t, 2H, J=7.6Hz); 13C NMR (100MHz, CDCl3) δ 191.2, 170.3, 147.7, 135.8, 133.1, 129.9 (2C), 128.9 (2C), 123.3, 64.5, 56.6, 39.3, 29.8, 29.1, 27.3, 24.4, 21.0; IR (ATR, vv [cm−1]): 3058, 3031, 2943, 2860, 1734, 1678, 1639, 1444, 1228, 1161, 794, 714 (m); HPLC purity: 98percent (method I); ESI-MS: m/z 381.3 [M+H]+

105

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Stage #1: 1-bromo-2-methyl benzene With magnesium; iodine in tetrahydrofuran

T=20°C; 0.5 h; Stage #2: α-ketophenylacetic acid With sodium hydride in tetrahydrofuran

T=0 - 20°C; 21.5 h; Stage #3: With water in tetrahydrofuran; ethyl acetate

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Rx-ID: 24794243

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NOVARTIS AG; NOVARTIS PHARMA GMBH

Patent: WO2006/48225 A1, 2006 ; Location in patent: Page/Page column 21 ; Title/Abstract Full Text Show Details

Intermediate M; Hydroxy-phenyl-o-tolyl-acetic acid; To a stirred suspension of magnesium (0.773 g, 31.81 mmol), iodine (cat. Amount) in THF (20 ml) is added dropwise, bromotoluene (3.83 ml, 31.81 mmol) in THF (30 ml). The reaction mixture is warmed to initiate the reaction and then allowed to stir at room temperature for 30 minutes. Meanwhile, a second mixture comprising benzoyl formic acid (4.342 g, 28.92 mmol) in THF (50 ml) is cooled in an ice bath. Sodium hydride (1.156 g of a 60percent dispersion in mineral oil, 28.92 mmol) is added to the mixture, portionwise, ensuring the temperature does not rise above 10 0C. Then the grignard reagent which has been stirring for 30 minutes is added dropwise and the reaction mixture is allowed to warm to room temperature. After stirring for 21 hours, the reaction mixture is partitioned between ethyl acetate (150 ml) and water (150 ml). The aqueous layer is acidified to pH 1 with 1 M hydrochloric acid and then extracted with ethyl acetate. The organic portions are combined, washed with brine, dried over MgSO4 and concentrated in vacuo. The crude residue is purified by chromatography on silica (eluting with ethyl acetate) to yield the titled compound. A

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106

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Rx-ID: 27994460

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A: 15% B: 56%

With quinoline; 1,10-phenanthroline; tris-(o-tolyl)phosphine; copper(I) bromide in 1-methyl-pyrrolidin-2one; quinoline

T=170°C; 16 h;

Goossen, Lukas J.; Rudolphi, Felix; Oppel, Christoph; Rodriguez, Nuria

Angewandte Chemie - International Edition, 2008 , vol. 47, # 16 p. 3043 - 3045 Title/Abstract Full Text View citing articles Show Details

107

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Rx-ID: 29056987

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53%

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With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine in N,N-dimethyl-formamide

T=0 - 20°C; Inert atmosphere; Hide Experimental Procedure

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Knust, Henner; Nettekoven, Matthias; Pinard, Emmanuel; Roche, Olivier; Rogers-Evans, Mark

Patent: US2009/312314 A1, 2009 ; Location in patent: Page/Page column 23 ; Title/Abstract Full Text Show Details

20.d.4:

To a solution of (3,4-dimethyl-phenyl)-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-amine (172 mg, 0.58 mmol) in DMF (4 mL) was added under a nitrogen atmosphere at 0° C. benzoylformic acid (105 mg, 0.70 mmol), 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyl-uronium tetrafluoroborate (280 mg, 0.88 mmol) and N,N-diisopropyl ethyl amine (299 μl, 1.75 mmol). The resulting solution was stirred for 18 h at ambient temperature. It was diluted with TBME (15 mL) and washed with aqueous hydrochloric acid (1 M, 15 mL), water (15 mL), aqueous Na2CO3 (saturatedm, 15 mL) and brine (15 mL). The combined aqueous layers were extracted with TBME (15 mL) and the combined organic layers dried over sodium sulfate. Concentration and purification by chromatography (SiO2, heptane:ethyl acetate=95:5 to 60:40) afforded the title compound (132 mg, 53percent) as a light brown oil. MS m/e: 427.2 [M+H]+.

108

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Rx-ID: 29425854

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68.12%

in acetic anhydride

T=150°C; 2 h;

Thale, Pranila B.; Borase, Pravin N.; Shankarling, Ganapati S.

Dalton Transactions, 2015 , vol. 44, # 31 p. 13947 - 13954 Title/Abstract Full Text View citing articles Show Details

67%

Stage #1: With sodium hydride in 1,4-dioxane

T=100°C; Perkin reaction; 0.5 h; Stage #2: With acetic anhydride in 1,4-dioxane

Perkin reaction;

Shih, Hsiencheng; Shih, Renshuay J.; Carson, Dennis A.

Journal of Heterocyclic Chemistry, 2011 , vol. 48, # 6 p. 1243 - 1250 Title/Abstract Full Text View citing articles Show Details

37%

With triethylamine in acetic anhydride

6 h; Reflux; Hide Experimental Procedure

Metacine, Inc.; Park, Bae Keun; Yoon, Sung-Hwa; Park, Ju-Young; Park, Sung Hoon

Patent: US2014/31563 A1, 2014 ; Location in patent: Paragraph 0202 ; Title/Abstract Full Text Show Details

1.1:(1) 3,4-diphenylfuran-2,5-dione (3)

[0202] After dissolving compound 2 (19.6 g, 96.0 mmol) in acetic anhydride (250 ml), Compound 1 (18.0 g, 80.0 mmol) is added thereto. After 6 hours of reaction with reflux, the temperature was reduced to room temperature, three times extractions were carried out with EA and seven times washings were carried out with brine. Water was removed with anhydrous sodium sulfate and to remove the remaining phenyl acetic acid, the column chromatography was carried out with EA/HX (1/2). After the distillation under the reduced pressure for the removal of the solvents conducted, vacuum drying was carried out to obtain compound 3. [0203] pale solid(11.0 g, 37.0percent); mp 183-184° C.; IR (KBr, cm−1) 1756; 1H NMR (DMSO-d6) δ 7.437-7486 (m, 10H); 13C NMR (DMSO-d6) δ 127.355, 128.568, 129.243, 130.434, 138.170, 164.873. Hide Details

With acetic anhydride

Reflux;

Moon, Jong Taik; Jeon, Ji Young; Park, Hang Ah; Noh, Young-Soo; Lee, Kyung-Tae; Kim, Jungahn; Choo, Dong Joon; Lee, Jae Yeol

Bioorganic and Medicinal Chemistry Letters, 2010 , vol. 20, # 2 p. 734 - 737 Title/Abstract Full Text View citing articles Show Details

109

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Rx-ID: 32114788

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45%

Stage #1: With sulfuric acid in water

T=60°C; 1 h; Stage #2: With sodium hydroxide in water

Hide Experimental Procedure

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Carta, Antonio; Briguglio, Irene; Piras, Sandra; Corona, Paola; Boatto, Giampiero; Nieddu, Maria; Giunchedi, Paolo; Marongiu, Maria Elena; Giliberti, Gabriele; Iuliano, Filippo; Blois, Sylvain; Ibba, Cristina; Busonera, Bernardetta; La Colla, Paolo

Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 23 p. 7070 - 7084 Title/Abstract Full Text View citing articles Show Details

5.1.11. General procedure for preparation of pyrido[2,3-g]quinoxalines 3e-f, 4g-j and 5k-o

General procedure: A solution (15 mL) of the 6,7-diamino-8-chloroquinoline (6b) (3 mmol) in 1 M H2SO4 was added of 4.0 mmol 2-oxo-2-phenylacetaldehyde, benzyl, sodium 2-oxobutanoate or sodium 2-oxo-3-phenylpropanoate and heated at 60 °C under stirring for 1 h. After cooling the resulting precipitate was filtered, while the acid mothers were neutralized by 2 N NaOH, the solids obtained were gathered together, washed, dried and crystallized by ethanol to give the pyrido[2,3-g]quinoxalines 3e-f, 4g and 5n, respectively. In the same condition condensation of 6,7-diamino-8-chloroquinolin-4(1H)-one (6c) with 2-oxo-2-phenylacetic acid afforded the pyrido[2,3-g]quinoxaline 5o. On the contrary, the reaction of 6b with ethyl 3-methyl-2-oxobutanoate, diethyl 2-methyl-3-oxosuccinate or 2-oxo-2-phenylacetic acid, gave the mixture 4h/5k; 4i/5l; 4j/5m, respectively, that were resolved by chromatography on silica gel column eluting with a mixture of diethyl ether/acetone in the ratio of 8:2.

110

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Rx-ID: 36217055

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48%

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With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride in dichloromethane

T=20°C; 5 h; Cooling with ice; Hide Experimental Procedure

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Mahaveer; Kulkarni; Radakrishna; Chandrashekar; Achaiah

Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013 , vol. 52, # 6 p. 818 - 823 Title/Abstract Full Text View citing articles Show Details

Coupling of amines and acids 6a-i (Scheme I)

General procedure: To a well stirred and ice cooled mixture of 3a-c (1.1 eq), EDCI (1.2 eq), and HOBt (1.2 eq) in dry DCM was added a solution of free amine 5a-c (1 eq) in dry DCM. After 5 hr stirring at RT the reaction mixture was washed with 1N H2S04, H20 and sat. NaHC03. The organic layer was dried (anhydrous MgS04) and solvent evaporated under vacuum. The residue was passed over silica-gel using Hexane:EtOAc to obtain the desired product25.

111

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Rx-ID: 37066913

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93%

in water

T=50 - 60°C; 2 h; Hide Experimental Procedure

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Tintas, Mihaela Liliana; Diac, Andreea Petronela; Soran, Albert; Terec, Anamaria; Grosu, Ion; Bogdan, Elena

Journal of Molecular Structure, 2014 , vol. 1058, # 1 p. 106 - 113 Title/Abstract Full Text View citing articles Show Details

2:General procedure

General procedure: A solution of 1 (5.2 mmol) in water (60 mL) was added dropwise(over 1–2 h) under vigorous stirring to a solution of hydrazide2 (5.2 mmol) in water (60 mL) heated to 50–60° C. The mixture was stirred for additional 2 h, and then cooled on an ice bath untilthe complete precipitation of the white solid. After filtration, the solid was successively washed with cold water and cold diethylether (or 2-propanol). The hydrazones have been used in the next step without further purification.

112

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Rx-ID: 37066914

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96%

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Tintas, Mihaela Liliana; Diac, Andreea Petronela; Soran, Albert; Terec, Anamaria; Grosu, Ion; Bogdan, Elena

Journal of Molecular Structure, 2014 , vol. 1058, # 1 p. 106 - 113 Title/Abstract Full Text View citing articles Show Details

in water

T=50 - 60°C; 2 h; Hide Experimental Procedure

3:General procedure

113

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Rx-ID: 37066916

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94%

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Tintas, Mihaela Liliana; Diac, Andreea Petronela; Soran, Albert; Terec, Anamaria; Grosu, Ion; Bogdan, Elena

Journal of Molecular Structure, 2014 , vol. 1058, # 1 p. 106 - 113 Title/Abstract Full Text View citing articles Show Details

in water

T=50 - 60°C; 2 h; Hide Experimental Procedure

4:General procedure

A solution of 1 (5.2 mmol) in water (60 mL) was added dropwise(over 1–2 h) under vigorous stirring to a solution of hydrazide2 (5.2 mmol) in water (60 mL) heated to 50–60° C. The mixture was stirred for additional 2 h, and then cooled on an ice bath untilthe complete precipitation of the white solid. After filtration, the solid was successively washed with cold water and cold diethylether (or 2-propanol). The hydrazones have been used in the nextstep without further purification.

114

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Rx-ID: 37066918

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92%

Tintas, Mihaela Liliana; Diac, Andreea Petronela; Soran, Albert; Terec, Anamaria; Grosu, Ion; Bogdan, Elena

Journal of Molecular Structure, 2014 , vol. 1058, # 1 p. 106 - 113 Title/Abstract Full Text View citing articles Show Details

in water

T=50 - 60°C; 2 h; Hide Experimental Procedure

5:General procedure

115

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Rx-ID: 37066920

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95%

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Tintas, Mihaela Liliana; Diac, Andreea Petronela; Soran, Albert; Terec, Anamaria; Grosu, Ion; Bogdan, Elena

Journal of Molecular Structure, 2014 , vol. 1058, # 1 p. 106 - 113 Title/Abstract Full Text View citing articles Show Details

in water

T=50 - 60°C; 2 h; Hide Experimental Procedure

6:General procedure

116

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Rx-ID: 37066922

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91%

in water

T=50 - 60°C; 2 h; Hide Experimental Procedure

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Tintas, Mihaela Liliana; Diac, Andreea Petronela; Soran, Albert; Terec, Anamaria; Grosu, Ion; Bogdan, Elena

Journal of Molecular Structure, 2014 , vol. 1058, # 1 p. 106 - 113 Title/Abstract Full Text View citing articles Show Details

7:General procedure

117

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Rx-ID: 39180154

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28%

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With dipotassium peroxodisulfate; silver nitrate in water; dimethyl sulfoxide

T=20°C; 24 h; Inert atmosphereSchlenk techniqueSealed tube; regioselective reaction; Hide Experimental Procedure

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Wang, Hua; Zhou, Shi-Liu; Guo, Li-Na; Duan, Xin-Hua

Tetrahedron, 2015 , vol. 71, # 4 p. 630 - 636 Title/Abstract Full Text View citing articles Show Details

1:4.3. General procedure for the decarboxylative acylation of coumarins with α-oxocarboxylic acids

General procedure: A 10mL oven-dried Schlenk-tube was charged with AgNO3 (3.4mg, 10molpercent), coumarin (1, 0.2mmol, 1.0equiv), and K2S2O8 (108mg, 0.4mmol, 2.0equiv). The tube was evacuated and backfilled with nitrogen (three times). α-Oxocarboxylic acids (2, 0.48mmol, 2.4equiv) in DMSO/H2O (1:1) 2mL were added by syringe. The tube was then sealed and the mixture was stirred for 24h at room temperature. Upon completion of the reaction, the mixture was diluted with EtOAc, filtered through a pad of Celite, and the filtrate was then removed under vacuo. The residue was purified with chromatography column on silica gel (gradient eluent of EtOAc/petroleum ether: 1:30 to 1:15) to give the corresponding products 3 or 4 in yields listed in Tables 2 and 3.

118

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Rx-ID: 39374523

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35.4%

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Stage #1: α-ketophenylacetic acid With oxalyl dichloride; N,N-dimethyl-formamide in dichloromethane

T=20°C; 4 h; Stage #2: (+)-phenylisopropylamine With triethylamine in dichloromethane

T=0 - 20°C; 1 h; Hide Experimental Procedure

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He, Ming-Hui; Su, Mei-Lin; Yu, Zhao-Hui; Chen, Guang-Xue; Zeng, Zhao-Hua; Yang, Jian-Wen

Chinese Chemical Letters, 2015 , vol. 26, # 1 p. 21 - 25 Title/Abstract Full Text View citing articles Show Details

N-Isopropylbenzoylformanilide (BFA-iPA):

To a CH2Cl2 solution (20mL) of benzoylformic acid (3.00g, 30.0mmol) prepared from methyl benzoylformate by basic hydrolysis with aqueous NaOH solution (quantitative) was added catalytic amount of DMF (1 drop) and oxalyl chloride (1.9mL, 22.0mmol). The reaction mixture was stirred for 4h at room temperature until generation of gases stopped and then cooled to 0°C. To this was added a solution of N-isopropylanilin (3.2mL, 29.9mmol) and Et3N (7.0mL, 50.2mmol). The reaction mixture was stirred at room temperature for 1h and then quenched by adding water. Organic materials were extracted 3 times with ethyl acetate, and then the combined extracts were washed successively with a 5percent HCl aqueous solution and saturated NaCl solution, dried over anhydrous MgSO4, evaporated to give the corresponding product, and recrystallized from ethyl acetate to give colorless crystals. Yield: 35.4percent. lH NMR (300MHz, CDCl3): δ 1.22–1.24 (d, 6H, J=6.0Hz), 5.01–5.15 (m, 1H, J=6.0Hz), 7.05–7.78 (m, 10H). 13C NMR (300MHz, CDCl3): δ 21.2, 47.0, 128.8, 129.1, 129.4, 131.2, 133.8, 134.2, 135.7, 166.8, 190.0. Anal. calcd. for C17H17NO2: C, 76.38; H, 6.41; N, 5.24percent. Found: C, 75.89; H, 6.50; N, 5.16.

119

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Rx-ID: 39861847

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49%

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With tert -butyl hydrogen peroxide; tetra-(n-butyl)ammonium iodide in decane; benzene

T=20 - 90°C; 12 h; Schlenk technique; Hide Experimental Procedure

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Mo, Hanjie; Chen, Dingben; Xu, Lingzhen; Chen, Di; Pan, Fuyou; Yang, Jianguo

Synthesis (Germany), 2015 , vol. 47, # 2 p. 209 - 215 Title/Abstract Full Text View citing articles Show Details

(B) Typical experimental procedureGeneral experimental procedures for the TBAI-catalyzed synthesis ofcyclohex-2-enyl benzoate

General procedure: An over-dried Schlenk tube was charged with tetrabutylammonium iodide (TBAI) (0.1 mmol),phenylglyoxylic acid (1a) (0.5 mmol) and cyclohexene (2a) (1.5 mmol) in benzene (2 mL) wasadded, Then tert-butyl hydroperoxide (1.25 mmol, 5~6 M in decane) was added dropwise into themixture at room temperature. The resulting mixture was stirred at 90 °C for 12 h. Then, the cooledreaction mixture was dissolved in water (5 mL) and extracted with CH2Cl2 (3×5 mL). Thecombined organic layer was dried with anhydrous MgSO4, and the product was further purified bysilica gel column chromatography and eluted with ethyl acetate and petroleum ether mixture toafford the product.

120

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Rx-ID: 40545761

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90%

With 9,10-dicyanoanthracene; potassium carbonate in chloroform

T=20°C; 24 h; Schlenk techniqueInert atmosphereIrradiation;

Yang, Chen; Yang, Jin-Dong; Li, Yi-He; Li, Xin; Cheng, Jin-Pei

Journal of Organic Chemistry, 2016 , vol. 81, # 24 p. 12357 - 12363 Title/Abstract Full Text Show Details

77%

With Ir(2-(2,4-difluorophenyl)-5-(trifluoromethyl)pyridine)2(4,4’-di-tert-butyl-2,2’-bipyridine)PF6; caesium carbonate in dichloromethane

T=20°C; 4 h; Molecular sieveIrradiationSchlenk technique;

Zhou, Quan-Quan; Guo, Wei; Ding, Wei; Wu, Xiong; Chen, Xi; Lu, Liang-Qiu; Xiao, Wen-Jing

Angewandte Chemie - International Edition, 2015 , vol. 54, # 38 p. 11196 - 11199 Angew. Chem., 2015 , vol. 127, p. 11348 - 11351,4 Title/Abstract Full Text View citing articles Show Details

66%

With 1-hydroxy-1,2-benzodioxol-3-(1H)-one in toluene

T=20°C; 8 h; Irradiation;

Tan, Hui; Li, Hongji; Ji, Wangqin; Wang, Lei

Angewandte Chemie - International Edition, 2015 , vol. 54, # 29 p. 8374 - 8377 Angew. Chem., 2015 , vol. 127, p. 8494 - 8497,4 Title/Abstract Full Text View citing articles Show Details

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63%

With dipotassium peroxodisulfate in water; acetonitrile

T=50°C; 24 h; Inert atmosphereSealed tube;

Wang, Hua; Guo, Li-Na; Wang, Shun; Duan, Xin-Hua

Organic Letters, 2015 , vol. 17, # 12 p. 3054 - 3057 Title/Abstract Full Text View citing articles Show Details

51%

With dipotassium peroxodisulfate in water; acetonitrile

T=50°C; 12 h; Inert atmosphereSchlenk techniqueSealed tube;

Wang, Peng-Fei; Feng, Yi-Si; Cheng, Zhi-Fei; Wu, Qiu-Min; Wang, Guang-Yu; Liu, Liang-Liang; Dai, Jian-Jun; Xu, Jun; Xu, HuaJian

Journal of Organic Chemistry, 2015 , vol. 80, # 18 p. 9314 - 9320 Title/Abstract Full Text View citing articles Show Details

121

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Rx-ID: 40545884

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63%

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Zhang, Xiaoyan; Song, Guiting; Cui, Hailei; Xu, Zhigang; Zhu, Jin; Chen, Zhongzhu

Science China Chemistry, 2015 , vol. 58, # 7 p. 1239 - 1242 Title/Abstract Full Text View citing articles Show Details

Stage #1: in methanol

T=50°C; Stage #2: With ammonium acetate in acetic acid

T=150°C; 0.166667 h; Microwave irradiation; Hide Experimental Procedure

2 Experimental

General procedure: General procedures for compounds 10 and 15 are as follows:a solution of aldehyde (0.50 mmol) and amine (0.50 mmol)in MeOH (1 mL) was stirred at room temperature for 10min in a 5 mL microwave vial. Next, acid (0.50 mmol) andisonitrile (0.50 mmol) were added separately. The mixturewas stirred at room temperature overnight. The reaction wasmonitored by TLC and the solvent was removed under nitrogenblowing. The residue was dissolved in AcOH (3 mL)and NH4AcO (2.5 mmol, 193 mg) was added and thentreated in microwave (MW) at 150 °C for 10 min. The solventwas removed under reduced pressure and the residuewas diluted with EtOAc (15 mL) and washed with sat. sodiumcarbonate and brine. The organic layer was dried overMgSO4 and concentrated. The residue was purified by silicagel column chromatography using a gradient of ethylacetate/hexane (1percent–100percent) to afford the relative products 9and 14a–14h.

122

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Rx-ID: 40545893

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56%

Stage #1: in methanol

T=50°C; Stage #2: With ammonium acetate in acetic acid

T=150°C; 0.166667 h; Microwave irradiation; Hide Experimental Procedure

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Zhang, Xiaoyan; Song, Guiting; Cui, Hailei; Xu, Zhigang; Zhu, Jin; Chen, Zhongzhu

Science China Chemistry, 2015 , vol. 58, # 7 p. 1239 - 1242 Title/Abstract Full Text View citing articles Show Details

2 Experimental

123

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Rx-ID: 41355137

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53%

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Stage #1: Benzoylformic acid With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride in dichloromethane

T=0°C; 0.166667 h; Stage #2: With 1- hydroxybenzotriazole in dichloromethane

T=0°C; 0.166667 h; Stage #3: 9b-amino-4b-hydroxy-7,8-dimethyl-4bH-indeno[1,2-b] benzofuran-10(9bH)-one in dichloromethane

T=0 - 20°C; 12 h; Hide Experimental Procedure

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Korea Research Institute of Chemical Technology; Katholieke Universiteit Leuven K.U. Leuven RandD; JUNG, Young Sik; HAN, Soo Bong; LEE, Chong-Kyo; KIM, Hae Soo; SHIN, Jin Soo; JOHAN, Neyts; HENDRIK, Jan Thibaut; MALPANI, Yashwardhan Radhamohan

Patent: EP2933254 A1, 2015 ; Location in patent: Paragraph 0072; 0073 ; Title/Abstract Full Text Show Details

12:<Example 12> Preparation of N-(4b-hydroxy-7,8-dimethyl-10-oxo-9b, 10-dihydro-4bH-indeno [1, 2-b] benzofuran-9b-yl)-2-oxo-2-phenyl acetamide

<Example 12> Preparation of N-(4b-hydroxy-7,8-dimethyl-10-oxo-9b, 10-dihydro-4bH-indeno [1, 2-b] benzofuran-9b-yl)-2-oxo-2-phenyl acetamide After dissolving 2-oxo-2-phenyl acetate (281 mg, 1.0 mmol) in DCM (10.0 ml), the temperature is lowered to 0°C. After EDCI (230 mg, 1.2 mmol) is placed at 0°C, stirring is carried out for 10 min. After adding HOBt (162 mg, 1.2 mmol) at 0°C and then stirring for 10 min, 9b-amino-4b-hydroxy-7.8-dimethyl-4bH-indeno [1, 2-b] benzofuran-10 (9bH)-one (281 mg, 1.0 mol) is added at 0°C and then stirring is carried at room temperature for 12 hours. After washing with water, removing moisture with Na2SO4, concentrating under reduced pressured, and purifying in a column, the target compound (219 mg, 53percent) is obtained. 1H-NMR (300MHz, CDCl ) δ 2.17 (s, 3H), 2.19 (s, 3H), 4.87 (s, 1H), 6.68 (s, 1H), 7.18 (s, 1H), 7.42-7.47 (m, 2H), 7.55-7.64 (m, 2H), 7.80-7.85 (m, 2H), 8.01 (d, J=7.56 Hz, 1H), 8.11 (s, 1H) 8.26 (s, 1H), 8.29 (s, 1H); 3

413.86 [M+H] +, 826.98 [2M+H]+ for LCMS.

124

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Rx-ID: 42141600

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52%

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With dipotassium peroxodisulfate; palladium diacetate in 1,4-dioxane; acetic acid

T=80°C; 12 h; regioselective reaction; Hide Experimental Procedure

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Yao, Jia-Ping; Wang, Guan-Wu

Tetrahedron Letters, 2016 , vol. 57, # 15 p. 1687 - 1690 Title/Abstract Full Text View citing articles Show Details

2) General Procedures

General procedure: A mixture of N-nitrosoaniline 1 (0.3 mmol), α-oxocarboxylic acid 2 (0.45 mmol), Pd(OAc)2 (0.03 mmol, 6.9 mg), K2S2O8 (0.6 mmol, 162.3 mg) in 1,4-dioxane/AcOH (7 : 3, 3 mL) was stirred at 80 °C for 12 h. The mixture was filtered by a silica gel plug with ethyl acetate as the eluent and evaporated in vacuum. The residual was separated on a silica gel column with petroleum ether/ethyl acetate as the eluent to give the desired product 3 as a mixture of inseparable syn and anti isomers.

125

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Rx-ID: 10127134

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90%

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With 5-(2-hydroxyethyl)-4-methyl-3-(phenylmethyl)thiazolium chloride; 1,8-diazabicyclo[5.4.0]undec-7ene in methanol

T=70°C; 18 h;

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Myers, Michael C.; Bharadwaj, Ashwin R.; Milgram, Benjamin C.; Scheidt, Karl A.

Journal of the American Chemical Society, 2005 , vol. 127, # 42 p. 14675 - 14680 Title/Abstract Full Text View citing articles Show Details

126

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Rx-ID: 10858166

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95%

in ethanol

0.5 h; Hide Experimental Procedure

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TECHNION RESEARCH AND DEVELOPMENT FOUNDATION LTD.

Patent: WO2008/23357 A1, 2008 ; Location in patent: Page/Page column 67; Sheet 14/26 ; Title/Abstract Full Text Show Details

Phenylglioxalic acid (26.6 mmol) was mixed with o-phenylenediamine (40 mmol) and stirred in 40 ml of ethanol for 30 min. The reaction mixture was filtered to give, after evaporation of solvent, the crude product. Recrystallization from ethanol gave pure yellow crystalls in 95percent yield.1H NMR (SOO MHz, DMSO-d6) δ (ppm): 12.54 (s, IH), 8.27-8.24 (m, 2H), 7.8 (d, J= 8.1Hz, IH), 7.52-7.45 (m, 4H), 7.31-7.26 (m, 2H). 13C NMR (75 MHz, DMSOd6) δ (ppm): 154.6, 135.6, 132.0, 130.3, 130.2, 129.2, 128.8, 127.8, 123.4, 115.1.

95%

in ethanol

0.5 h; Hide Experimental Procedure

Gavish, Moshe; Veenman, Jehuda Arieh; Shterenberg, Alex; Marek, Ilan

Patent: US2010/29658 A1, 2010 ; Location in patent: Page/Page column 32 ; Title/Abstract Full Text Show Details

Phenylglioxalic acid (26.6 mmol) was mixed with o-phenylenediamine (40 mmol) and stirred in 40 ml of ethanol for 30 min. The reaction mixture was filtered to give, after evaporation of solvent, the crude product. Recrystallization from ethanol gave pure yellow crystalls in 95percent yield.1H NMR (300 MHz, DMSO-d6) δ (ppm): 12.54 (s, 1H), 8.27-8.24 (m, 2H), 7.8 (d, J=8.1 Hz, 1H), 7.52-7.45 (m, 4H), 7.31-7.26 (m, 2H). 13C NMR (75 MHz, DMSO-d6) δ (ppm ): 154.6, 135.6, 132.0, 130.3, 130.2, 129.2, 128.8, 127.8, 123.4, 115.1.

50%

in ethanol

T=20°C; 2 h; Hide Experimental Procedure

MERCK PATENT GMBH; RICHARDSON,Thomas E.

Patent: WO2014/121885 A1, 2014 ; Location in patent: Page/Page column 48 ; Title/Abstract Full Text Show Details

2.1:Example 2 - Synthesis of Compound 1 (2-PhenyI-3-quinolin-4-yl-quinoxaline)

Step 1 : A mixture of oxo-phenyl-acetic acid (500 mg, 3.33 mmol) and benzene- 1 ,2-diamine (792 mg, 7.33 mmol) in ethanol (15 mL) was stirred for 2 h at room temperature. The reaction became a homogeneous yellow solution, and then started a yellow solid started

precipitating.The reaction mixture was filtered. The solid was purified by chromatography using dichloromethane / ethyl acetate (0percent to 10percent) as eiuent to give 3-phenyl-quinoxalin-2-ol (370 mg; 50percent) as a yellow solid; LCMS (ESI) 223 (M+H); HPLC 100percent, RT: 2.14 min; 1H NMR (400 MHz, DMSO-d6) δ ppm: 12.57 (br s, 1 H), 8.25 - 8.36 (m, 1 H), 7.79 - 7.89 (m, 1 H), 7.43 - 7.59 (m, 3H), 7.26 - 7.39 (m, 2H).

127

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Rx-ID: 39861848

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38%

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With tert -butyl hydrogen peroxide; tetra-(n-butyl)ammonium iodide in decane; benzene

T=20 - 90°C; 12 h; Schlenk technique; Hide Experimental Procedure

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Mo, Hanjie; Chen, Dingben; Xu, Lingzhen; Chen, Di; Pan, Fuyou; Yang, Jianguo

Synthesis (Germany), 2015 , vol. 47, # 2 p. 209 - 215 Title/Abstract Full Text View citing articles Show Details

(B) Typical experimental procedureGeneral experimental procedures for the TBAI-catalyzed synthesis ofcyclohex-2-enyl benzoate

128

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Rx-ID: 40545758

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92%

With dipotassium peroxodisulfate in water; acetonitrile

T=50°C; 12 h; Inert atmosphereSchlenk techniqueSealed tube; Reagent/catalystTemperature;

Wang, Peng-Fei; Feng, Yi-Si; Cheng, Zhi-Fei; Wu, Qiu-Min; Wang, Guang-Yu; Liu, Liang-Liang; Dai, Jian-Jun; Xu, Jun; Xu, HuaJian

Journal of Organic Chemistry, 2015 , vol. 80, # 18 p. 9314 - 9320 Title/Abstract Full Text View citing articles Show Details

86%

With dipotassium peroxodisulfate in water; acetonitrile

T=50°C; 24 h; Inert atmosphereSealed tube; Reagent/catalystSolventTemperature;

Wang, Hua; Guo, Li-Na; Wang, Shun; Duan, Xin-Hua

Organic Letters, 2015 , vol. 17, # 12 p. 3054 - 3057 Title/Abstract Full Text View citing articles Show Details

61%

With [Ru(2,2′-bipyridine)3][hexafluorophosphate]2; 1-acetoxy-1H-1λ3-benzo[d][1,2]iodoxol-3-one in dichloromethane

T=25°C; 5 h; Sealed tubeInert atmosphereIrradiation; chemoselective reaction;

Huang, Hanchu; Zhang, Guojin; Chen, Yiyun

Angewandte Chemie - International Edition, 2015 , vol. 54, # 27 p. 7872 - 7876 Angew. Chem., 2015 , vol. 127, # 27 p. 7983 - 7987,5 Title/Abstract Full Text View citing articles Show Details

129

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Rx-ID: 40785414

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70%

With [NiCl2(1,2-dimethoxyethane)]; Ir(2-(2,4-difluorophenyl)-5-(trifluoromethyl)pyridine)2(4,4’-di-tert-butyl2,2’-bipyridine)PF6; lithium carbonate; dtbbpy in water; DMFA

72 h; Inert atmosphereIrradiation;

Chu, Lingling; Lipshultz, Jeffrey M.; Macmillan, David W. C.

Angewandte Chemie - International Edition, 2015 , vol. 54, # 27 p. 7929 - 7933 Angew. Chem., 2015 , vol. 127, # 27 p. 8040 - 8044,5 Title/Abstract Full Text View citing articles Show Details

70%

With [nickel(II)dichloride(dimethoxyethane)]; Ir[dF(CF3)ppy]2(dtbbpy)PF6; lithium carbonate; dtbbpy in water; DMFA

72 h; Inert atmosphereMicrowave irradiation; Hide Experimental Procedure

THE TRUSTEES OF PRINCETON UNIVERSITY; MACMILLAN, David, W.C.; ZUO, Zhiwei

Patent: WO2015/153381 A2, 2015 ; Location in patent: Page/Page column 32; 36; 37 ; Title/Abstract Full Text Show Details

36:EXAMPLE 36 - (4-Fluorophenyl)(phenyl)methanone

EXAMPLE 36 - (4-Fluorophenyl)(phenyl)methanone Prepared according to General Procedure B with l-fluoro-4-iodobenzene (275.0 mg, 2.5 mmol, 5.0 equiv) and L12CO3 (184.8 mg, 2.5 mmol, 5.0 equiv), purified with 5percent EtOAc in hexanes as eluent, to yield the product as a pale yellow solid, 70.2 mg, 70percent yield. NMR (501 MHz, Chloroform-rf) δ 7.90 - 7.81 (m, 2H), 7.79 - 7.74 (m, 2H), 7.62 - 7.56 (m, 1H), 7.49 (dd, J = 8.5, 7.1 Hz, 2H), 7.16 (t, J= 8.5 Hz, 2H). 13C NMR (126 MHz, CDCI3) δ 195.0, 165.3 (d, J= 264.3 Hz), 137.6, 133.2 (d, /= 2.7 Hz), 133.1 (d, J= 10.1 Hz), 132.7, 129.5, 128.1, 115.6. General procedure B for the decarboxylation arylation of keto acids iaryl halide scope"): An oven-dried 40 mL vial equipped with a Teflon septum cap and magnetic stir bar was charged with rr[dF(CF3)ppy]2(dtbbpy)PF6 (11.2 mg, 0.01 mmol, 0.02 equiv), NiC^ glyme (11.2 mg,

0.05 mmol, 0.10 equiv), 4,4'-di-tert-butyl-2,2'-bipyridine (20.1 mg, 0.075 mmol, 0.15 equiv), phenylglyoxylic acid (150 mg, 1.00 mmol, 2.0 equiv), the corresponding aryl halide (0.50 mmol, 1.0 equiv), and L12CO3 (73.9 mg, 1.00 mmol, 2.0 equiv) from a bottle stored in a dessicator. To this vial was added DMF (25 mL) and water (18 iL, 2.00 mmol, 2.0 equiv). The reaction mixture was degassed for 30 minutes by bubbling argon stream, then sealed with parafilm. The vial was irradiated with 34W Blue LED lamp (Kessil KSH150B LED Grow Light) for 72 hours with cooling from a fan (vial temperature reached 37 °C). After 72 hours, the reaction was diluted with 25 mL 0 and extracted with 3x75 mL Et20. The combined organic layers were washed with 3x25 mL 0, then dried over MgS(, filtered, and concentrated in vacuo.

130

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Rx-ID: 41406489

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97%

With Potassium peroxomonosulfate

T=65°C; 30 h; Hide Experimental Procedure

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Padala, Anil K.; Saikam, Varma; Ali, Asif; Ahmed, Qazi Naveed

Tetrahedron, 2015 , vol. 71, # 50 p. 9388 - 9395 Title/Abstract Full Text View citing articles Show Details

4.3 General procedure for preparation of esters (RCO2R′) 5 from 2-oxoacids (RCOCO2H) 3/2-oxoaldehydes (RCOCHO) 3 &/2-oxoesters (RCOCO2R″) 4

General procedure: A mixture of 2-oxoacids 2/2-oxoaldehydes 3/2-oxoesters 4 (0.5mmol), oxone (1.25mmol) and alcohol (1.5mL) in round bottomed flask was stirred at 65°C. After completion of the reaction that was confirmed by thin layer chromatography, the crude mixture was cooled to room temperature, filtered and purified by column chromatography using silica gel (100–200 ) with ethyl acetate and hexane as an eluent to afford the desired product 5 in 70–99 percent yields.

131

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Rx-ID: 43107986

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90%

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Meza-León, Rosa Luisa; Bernès, Sylvain; Cortés-López, Guadalupe Nallely; Mastranzo, Virginia M.; Sosa-Rivadeneyra, Martha; Sartillo-Piscil, Fernando

Tetrahedron Letters, 2016 , vol. 57, # 37 p. 4232 - 4234 Title/Abstract Full Text View citing articles Show Details

in dichloromethane

T=0°C; 2 h; Inert atmosphereIrradiation; Hide Experimental Procedure

Method for thesynthesis of 5-hydroxy hydantoins.

General procedure: To a solution of a-keto carboxylic acid (1 mmol) and carbodiimide (1 mmol) in 5 mL of dry CH2Cl2 at 0 °C under argon atmosphere. The reaction was irradiated with a visible light lamp of 150 watts, the solution was stirred for 2 h, as the disappearance of the a-keto carboxylic acid was monitoredby TLC. After warming to room temperature the reaction was filtered on a silicagel bed and then concentrated under vacuum.

132

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Rx-ID: 43107987

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85%

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Meza-León, Rosa Luisa; Bernès, Sylvain; Cortés-López, Guadalupe Nallely; Mastranzo, Virginia M.; Sosa-Rivadeneyra, Martha; Sartillo-Piscil, Fernando

Tetrahedron Letters, 2016 , vol. 57, # 37 p. 4232 - 4234 Title/Abstract Full Text View citing articles Show Details

in dichloromethane

T=0°C; 2 h; Inert atmosphereIrradiation; Hide Experimental Procedure

Method for thesynthesis of 5-hydroxy hydantoins.

133

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Rx-ID: 43201304

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42%

With tert.-butylhydroperoxide; sodium carbonate; potassium iodide in 1,4-dioxane

T=120°C; 5 h; Sealed tube; Hide Experimental Procedure

Gao, Peng; Wang, Juan; Bai, Zijing; Cheng, Hualei; Xiao, Jian; Lai, Mengnan; Yang, Desuo; Fan, Mingjin

Tetrahedron Letters, 2016 , vol. 57, # 41 p. 4616 - 4619 Title/Abstract Full Text Show Details

2.Experimental Procedures

General procedure: In a 35 mL sealed tube, a solution of 3 mL of 1,4-dioxane, acyhydrazines 1 (0.5mmol), α-ketoacids 2 (0.5 mmol) , Na2CO3 (0.6 mmol), KI (0.05 mmol) and TBHP (2.0 mmol) was sequentially added. The reaction mixture was stirred at 120 °C for 5 h and then cooled to room temperature. Then, the mixture extracted with ethyl acetate (2 × 10 mL), and the organic layer was combined and dried with anhydrous Na2SO4. After removal of the solvent under reduced pressure, the residue was separated by flash column chromatography to afford the pure product 3 (PE:EA = 20:1).

134

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Rx-ID: 43974240

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97%

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Sogang University Academic Cooperation; Haw, Nam Hwe; Lee, Byung Noh; Lee, Won Gu

Patent: KR101483445 B1, 2015 ; Location in patent: Paragraph 0468-0470 ;

in neat (no solvent, solid phase) T=50°C; 1 h; SolventTemperature; Hide Experimental Procedure

Title/Abstract Full Text Show Details

107:Example 107

5.2 g (50.0 mmol) of dimethylhydrazine-carbon dioxide ((CH3)2NH2+NH-CO2-) and 7.5 g (50.0 mmol) of 2-oxo-2-phenylacetic acid were reacted at 50 °C for 1 hour as a reactant, the remainder is the same as in Example 1. The obtained compound was (E) -2- (2,2dimethylhydrazino) -2-phenylacetic acid, the selectivity was 99percent, and the yield was 97percent.

135

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Rx-ID: 728427

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36.4%

in diethyl ether

T=0 - 20°C; 24.5 h; Hide Experimental Procedure

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Bodor, Nicholas S.

Patent: US2007/123557 A1, 2007 ; Location in patent: Page/Page column 9; 12; 15-16 ; Title/Abstract Full Text Show Details

Cyclopentylmagnesium bromide ether solution (100 ml, 2M; 0.2 mol) was added drop-wise to benzoylformic acid (15 g, 0.1 mol) in 330 ml of anhydrous ethyl ether at 0° C. The mixture was stirred at 0° C. for 30 min and at room temperature for 24 h. The reaction mixture was treated with 1 N HCl, and the aqueous solution was extracted with ether. The combined ether solution was treated with K2CO3 solution. The potassium carbonate solution was acidified with HCl and extracted with ether twice. The ether solution was dried with anhydrous sodium sulfate and evaporated to give a crude product. The crude product was washed with water to get pure racemic cyclopentylmandelic acid 1 (8.0 g, 36.4percent). Needle-like crystal, m.p.: 153-154° C. 1H NMR (CDCl3,300 MHz): 1.28-1.39, 1.42-1.50, 1.51-1.61, 1.63-1.72

[8H, m, (CH2)4], 2.93 [1H, p, CHC(OH)], 7.26-7.30, 7.33-7.36, 7.65-7.67(5H, m, Ph) ppm.; Cyclopentylmagnesium bromide ether solution (100 ml, 2M; 0.2 mol) was added drop-wise to benzoylformic acid (15 g, 0.1 mol) in 330 ml of anhydrous ethyl ether at 0° C. The mixture

was stirred at 0° C. for 30 min and at room temperature for 24 h. The reaction mixture was treated with 1 N HCl, and the aqueous solution was extracted with ether. The combined ether solution was treated with K2CO3 solution. The potassium carbonate solution was acidified with HCl and extracted with ether twice. The ether solution was dried with anhydrous sodium sulfate and evaporated to give a crude product. The crude product was washed with water to get pure racemic cyclopentylmandelic acid 1 (8.0 g, 36.4percent). Needle-like crystals, m.p.: 153-154° C. 1H NMR (CDCl3, 500 MHz): 1.28-1.39, 1.42-1.50, 1.51-1.61, 1.63-1.72 [8H, m, (CH2)4], 2.93 [1H, p, CHC(OH)], 7.26-7.30, 7.33-7.36, 7.65-7.67(5H, m, Ph) ppm.

36.4%

Wu; Mori; Buchwald; Bodor, Nicholas

Pharmazie, 2008 , vol. 63, # 3 p. 200 - 209 Title/Abstract Full Text View citing articles Show Details

Stage #1: in diethyl ether

T=0 - 20°C; 24.5 h; Stage #2: With hydrogenchloride in diethyl ether; water

Faust et al.

Journal of the American Chemical Society, 1959 , vol. 81, p. 2214,2218 Full Text Show Details

136

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Rx-ID: 728435

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93%

With phosphate buffer; D-glucose; 2-hydroxyethanethiol; sodium chloride; 1,4-dihydronicotinamide adenine dinucleotide; benzoylformate reductase in water; toluene

T=30°C; 48 h; Other catalysts: bovine serum albumin, yeast alcohol dehydrogenase, glucose dehydrogenase, formate dehydrogenase; Product distribution;

Yamazaki, Yoshimitsu; Maeda, Hidekatsu

Agricultural and Biological Chemistry, 1986 , vol. 50, # 10 p. 2621 - 2632 Title/Abstract Full Text Show Details

93%

With phosphate buffer; D-glucose; 2-hydroxyethanethiol; sodium chloride; formate dehydrogenase; 1,4dihydronicotinamide adenine dinucleotide; benzoylformate reductase; bovine serum albumin; yeast alcohol dehydrogenase in ethanol; water; toluene

T=30°C; 48 h;

Yamazaki, Yoshimitsu; Maeda, Hidekatsu

Agricultural and Biological Chemistry, 1986 , vol. 50, # 10 p. 2621 - 2632 Title/Abstract Full Text Show Details

With fermenting yeast

Neubauer; Fromherz

Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1910 , vol. 70, p. 342 Full Text Show Details

Hide Details

With milk

Rosenthaler

Chem. Zentralbl., 1910 , vol. 81, # II p. 1671 Full Text Show Details

With sodium tetrahydroborate; 1a in aq. HCl

2.) 0 deg C, 2 h;; Multistep reaction;

Takahashi; Odashima; Koga

Chemical and Pharmaceutical Bulletin, 1985 , vol. 33, # 8 p. 3571 - 3573 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 0 °C 1.2: tetrahydrofuran / 10 h / 20 °C 2.1: H2O2; aq. NaOH / tetrahydrofuran View Scheme

Ramachandran, P. Veeraraghavan; Pitre, Sangeeta; Brown, Herbert C.

Journal of Organic Chemistry, 2002 , vol. 67, # 15 p. 5315 - 5319 Title/Abstract Full Text View citing articles Show Details

With yeast alcohol dehydrogenase from Saccharomyces cerevisiae; NADH

T=25°C; pH=7; aq. phosphate bufferEnzymatic reaction;

Li, Gui-Yin; Zhou, Zhi-De; Li, Yuan-Jian; Huang, Ke-Long; Zhong, Ming

Journal of Magnetism and Magnetic Materials, 2010 , vol. 322, # 24 p. 3862 - 3868 Title/Abstract Full Text View citing articles Show Details

With (R)-ketoacid reductase from Saccharomyces cerevisiae ZJB

Xue, Ya-Ping; Zheng, Yu-Guo; Zhang, Ya-Qin; Sun, Jing-Lei; Liu, Zhi-Qiang; Shen, Yin-Chu

; glycerol in aq. phosphate buffer

5074

T=30°C; pH=7.5; Enzymatic reaction; Reagent/catalyst; enantioselective reaction;

Chemical Communications, 2013 , vol. 49, # 91 p. 10706 - 10708 Title/Abstract Full Text View citing articles Show Details

With glucose dehydrogenase; alpha-D-glucopyranose; BgADH2 enzyme; nicotinamide adenine dinucleotide phosphate in water

T=30°C; pH=6.5; Enzymatic reaction; enantioselective reaction;

Chen, Xiang; Liu, Zhi-Qiang; Huang, Jian-Feng; Lin, Chao-Ping; Zheng, Yu-Guo

Chemical Communications, 2015 , vol. 51, # 61 p. 12328 - 12331 Title/Abstract Full Text View citing articles Show Details

With potassium tert-butylate; hydrogen in ethanol

T=20°C; P=11400.8 Torr; 24 h; Inert atmosphereAutoclave; Reagent/catalystSolvent; Hide Experimental Procedure

Zhejiang Jiuzhou Pharmaceutical Co., Ltd.; Yan, Pucha; Che, Daqing; Lin, Yuanqiang; Zhang, Xiangdong; Chen, Kang; Yan, Yongliang

Patent: CN105481677 A, 2016 ; Location in patent: Paragraph 0031; 0032; 0033; 0037 ; Title/Abstract Full Text Show Details

1:Example 1: Preparation of 2-hydroxy-2-phenylacetic acid

Under nitrogen, the inner tube was added 200mL hydrogenation a- keto acid substrate 2a (3g, 20mmol), potassium tert-butoxide (112 mg, 1mmol), catalyst M (20mg, 0.02mmol, R = 3- methyl ) and a solvent (50mL). The inside of the reaction tube into the autoclave. After the replacement with hydrogen gas in the autoclave, an initial charge to 15 atmospheres hydrogen pressure, and allowed the reaction was stirred at room temperature for 24 hours. The hydrogenation reaction, hydrogen was released, the autoclave was opened. The reaction mixture was filtered to remove the catalyst by rapid short silica gel using NMR analysis of the reaction conversion

137

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Rx-ID: 3409278

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82%

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With 4-(N,N-dimethlyamino)pyridine; dicyclohexyl-carbodiimide in dichloromethane

T=25°C; 1 h;

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Tripathy, Rabindranath; Carroll, Patrick J.; Thornton, Edward R.

Journal of the American Chemical Society, 1991 , vol. 113, # 20 p. 7630 - 7640 Title/Abstract Full Text View citing articles Show Details

138

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Rx-ID: 27994478

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26%

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With quinoline; 1,10-phenanthroline; tris-(o-tolyl)phosphine; copper(I) bromide in 1-methyl-pyrrolidin-2one; quinoline

T=170°C; 16 h;

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Goossen, Lukas J.; Rudolphi, Felix; Oppel, Christoph; Rodriguez, Nuria

Angewandte Chemie - International Edition, 2008 , vol. 47, # 16 p. 3043 - 3045 Title/Abstract Full Text View citing articles Show Details

139

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Rx-ID: 28129565

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27%

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With 1- hydroxybenzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N,Ndiisopropylethylamine in dichloromethane

T=0 - 20°C; 23.3333 h; Hide Experimental Procedure

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Knust, Henner; Nettekoven, Matthias; Pinard, Emmanuel; Roche, Olivier; Rogers-Evans, Mark

Patent: US2009/36422 A1, 2009 ; Location in patent: Page/Page column 88 ; Title/Abstract Full Text Show Details

218.2:

Step 2: N-(3,4-Dimethyl-phenyl)-2-oxo-2-phenyl-N-[2-(4-trifluoromethyl-phenyl)-ethyl]-acetamide To a solution of (3,4-dimethyl-phenyl)-[2-(4-trifluoromethyl-phenyl)-ethyl]-amine (5.00 g, 17.0 mmol) and benzoylformic acid (2.61 g, 17.0 mmol) in dichloromethane (110 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (3.67 g, 18.8 mmol), 1hydroxybenzotriazole (235 mg, 1.70 mmol) and N-ethyldiisopropylamine (4.5 mL, 25.6 mmol) at 0° C. After stirring for 20 min at 0° C., the reaction mixture was allowed to reach ambient temperature and stirring was continued for 23 h. The mixture was washed with aqueous sodium carbonate (half-saturated, 100 mL), aqueous HCl (1 M, 100 mL) and brine (100 mL). The aqueous layers were washed with dichloromethane (100 mL). The combined organic layers were dried over sodium sulfate. Concentration and purification by chromatography (SiO2, heptane:ethyl acetate=80:20) afforded the title compound (1.96 g, 27percent) as a light-yellow oil. MS m/e: 426.1 [M+H]+.

140

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Rx-ID: 36217029

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28%

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With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride in dichloromethane

T=20°C; 5 h; Cooling with ice; Hide Experimental Procedure

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Mahaveer; Kulkarni; Radakrishna; Chandrashekar; Achaiah

Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013 , vol. 52, # 6 p. 818 - 823 Title/Abstract Full Text View citing articles Show Details

Coupling of amines and acids 6a-i (Scheme I)

141

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Rx-ID: 37095000

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61%

With tris(1,10-phenanthroline)ruthenium(II) dichloride; oxygen in dimethyl sulfoxide

T=32°C; 36 h; IrradiationSchlenk technique;

Liu, Jie; Liu, Qiang; Yi, Hong; Qin, Chu; Bai, Ruopeng; Qi, Xiaotian; Lan, Yu; Lei, Aiwen

Angewandte Chemie - International Edition, 2014 , vol. 53, # 2 p. 502 - 506 Angew. Chem., 2014 , vol. 126, # 2 p. 512 - 516,5 Title/Abstract Full Text View citing articles Show Details

58%

With water; oxygen in 1,4-dioxane

T=20°C; 48 h; Schlenk techniqueIrradiation;

Xu, Wen-Tao; Huang, Bei; Dai, Jian-Jun; Xu, Jun; Xu, Hua-Jian

Organic Letters, 2016 , vol. 18, # 13 p. 3114 - 3117 Title/Abstract Full Text View citing articles Show Details

56%

With silver trifluoromethanesulfonate in water; acetonitrile

T=60°C; 24 h; Schlenk technique;

Xu, Xiao-Lan; Xu, Wen-Tao; Wu, Ji-Wei; He, Jian-Bo; Xu, Hua-Jian

Organic and Biomolecular Chemistry, 2016 , vol. 14, # 42 p. 9970 - 9973 Title/Abstract Full Text Show Details

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48%

Stage #1: Benzoylformic acid With potassium tert-butylate in ethanol

T=20°C; 2 h; Sealed tube; Stage #2: aniline With dipotassium peroxodisulfate in acetonitrile

T=80°C; 24 h; Sealed tubeInert atmosphere;

Laha, Joydev K.; Patel, Ketul V.; Satyanarayana Tummalapalli; Dayal, Neetu

Chemical Communications, 2016 , vol. 52, # 67 p. 10245 - 10248 Title/Abstract Full Text View citing articles Show Details

142

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Rx-ID: 41355138

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30%

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Stage #1: Benzoylformic acid With 1- hydroxybenzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)carbodiimide hydrochloride in dichloromethane; DMFA

T=0 - 20°C; Stage #2: 9b-amino-4b-hydroxy-7-isopropyl-4-nitro-4bH-indeno[1,2-b]benzofuran-10(9bH)-one in dichloromethane; DMFA

T=20°C; Hide Experimental Procedure

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Patent: EP2933254 A1, 2015 ; Location in patent: Paragraph 0080; 0081 ; Title/Abstract Full Text Show Details

16:<Example 16> Preparation of N-(4b-hydroxy-7-isopropyl-4-nitro-10-oxo-9b, 10-dihydro-4bH-indeno[1,2-b]benzofuran-9b-yl)-2-oxo-2-phenyl acetamide

<Example 16> Preparation of N-(4b-hydroxy-7-isopropyl-4-nitro-10-oxo-9b, 10-dihydro-4bH-indeno[1,2-b]benzofuran-9b-yl)-2-oxo-2-phenyl acetamide After adding phenyl glyoxalic acid (155 mg, 1.03 mmol) in DMF : DCM (1 : 2 10 ml), EDCI (296 mg, 1.54 mmol) is added at 0°C. After adding 1-hydroxy benzotrinaole (205 mg, 1.54 mmol), stirring is carried out at room temperature for 15 - 30 min.

After adding 9b-amino-4b-hydroxy-7-isopropyl-4-nitro-4bH-indeno [1, 2-b] benzofuran-10 (9bH)-one (300 mg, 1.03 mmol), stirring is carried out at room temperature overnight. The organic layers separated using water (100 ml) and ethyl acetate (70 ml x 3) are collected and washed with water (50 ml) and brine (50 ml) in that order. After removing moisture with anhydrous sodium sulfate and then concentrating, purification is carried out in a flash silica gel column chromatography (25percent ethyl acetate hexane) to obtain the target compound (125 mg, 30percent). 1H-NMR (300 MHz, CDCI ) δ 1.19 (dd, J = 3.3 Hz, J = 6.9 Hz, 6H, CH3), 2.86 (sept, J = 6.9 Hz, 1H, CH), 6.50 (s, 1H, OH), 6.73 (s, 1H, ArH), 6.94 (d, J = 7.8 Hz, 1H, ArH), 7.41-7.49 (m, 3H, ArH), 7.58-7.63 (m, 2H, ArH+NH), 7.77-7.82 (m, 1H, ArH), 8.26-8.29 (m, 3H, ArH), 3

8.50 (dd, J = 8.1 Hz, J = 1 Hz, 1H, ArH); LCMS: 472.80 (M+H) +.

143

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Rx-ID: 41355139

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27%

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With 1- hydroxybenzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine in dichloromethane

T=20°C; 24 h; Hide Experimental Procedure

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Patent: EP2933254 A1, 2015 ; Location in patent: Paragraph 0078; 0079 ; Title/Abstract Full Text Show Details

15:<Example 15> Preparation of N-(4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1, 2-b] benzofuran-9b-yl)-2-oxo-2-phenyl acetamide

<Example 15> Preparation of N-(4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1, 2-b] benzofuran-9b-yl)-2-oxo-2-phenyl acetamide After dissolving phenyl glyoxylic acid (0.30 g, 2.03 mmol) in anhydrous methylene chloride (10 ml), EDCI (0.38 g, 2.03 mmol), HOBt (0.27 g, 2.03 mmol), 3-(2-amino ethyl)-9b-amino-4b-hydroxy-7-isopropyl-4bH-indeno [1, 2-b] benzofuran-10 (9bH)-one (0.50 g, 1.69 mmol) and triethyl amine (0.25 g, 2.53 mmol) are added and stirring is carried out at room temperature for 24 hours. After diluting with methylene chloride and washing with water several times, the organic layer is dried and filtered. After purifying in a column chromatography (ethyl acetate : hexane = 1 : 2), the target compound (0.20 g, 27percent) is obtained. 1H-NMR (300 MHz, CDCl ) δ 1.16-1.19 (dd, J=6.9, 3.0Hz, 2H, CH2) 2.77-2.89(m, 1H, CH) 4.93(s, 1H, OH) 6.75(s, 1H, NH) 6.87(d, J=7.8Hz, 1H, ArH) 7.44(t, J=8.1Hz, 2H, ArH) 7.57-7.64(m, 3H, ArH) 7.85(m, 1H, ArH) 8.02(d, J=7.5Hz, 1H, ArH) 8.09(s, 1H, ArH). 3

8.26(d, J=7.2Hz, 2H, ArH); MS (EI) m/e (rel. intensity) 428(M+H) +, 855(2M+H) + for LCMS.

144

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Rx-ID: 41406492

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80%

With Potassium peroxomonosulfate

T=65°C; 40 h; Hide Experimental Procedure

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Padala, Anil K.; Saikam, Varma; Ali, Asif; Ahmed, Qazi Naveed

Tetrahedron, 2015 , vol. 71, # 50 p. 9388 - 9395 Title/Abstract Full Text View citing articles Show Details

4.3 General procedure for preparation of esters (RCO2R′) 5 from 2-oxoacids (RCOCO2H) 3/2-oxoaldehydes (RCOCHO) 3 &/2-oxoesters (RCOCO2R″) 4

145

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Rx-ID: 41406493

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80%

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With Potassium peroxomonosulfate

T=65°C; 40 h; Hide Experimental Procedure

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Padala, Anil K.; Saikam, Varma; Ali, Asif; Ahmed, Qazi Naveed

Tetrahedron, 2015 , vol. 71, # 50 p. 9388 - 9395 Title/Abstract Full Text View citing articles Show Details

4.3 General procedure for preparation of esters (RCO2R′) 5 from 2-oxoacids (RCOCO2H) 3/2-oxoaldehydes (RCOCHO) 3 &/2-oxoesters (RCOCO2R″) 4

146

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Rx-ID: 41975310

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93%

With ammonium peroxydisulfate; palladium diacetate in diethylene glycol dimethyl ether

T=20°C; 18 h; Sealed tube; Catalytic behavior; Reagent/catalystSolventTemperature;

Wu, Yinuo; Sun, Lei; Chen, Yunyun; Zhou, Qian; Huang, Jia-Wu; Miao, Hui; Luo, Hai-Bin

Journal of Organic Chemistry, 2016 , vol. 81, # 3 p. 1244 - 1250 Title/Abstract Full Text View citing articles Show Details

89%

With dipotassium peroxodisulfate; palladium(II) trifluoroacetate in diethylene glycol dimethyl ether

T=80°C; 20 h; Inert atmosphere; Catalytic behavior; Reagent/catalystSolventTemperature; regioselective reaction; Hide Experimental Procedure

Zhang, Liang; Wang, Zhe; Guo, Peiyu; Sun, Wei; Li, Ya-Min; Sun, Meng; Hua, Chengwen

Tetrahedron Letters, 2016 , vol. 57, # 23 p. 2511 - 2514 Title/Abstract Full Text View citing articles Show Details

General catalytic procedure forortho-acylation of N-nitrosoaniline with α-keto acids.

General procedure: An oven-dried 10 mL screw-capped vial was charged with Pd(TFA)2 (6.6 mg, 0.02 mmol, 10 mol percent), N-methyl-N-nitrosoaniline (27.2 mg, 0.2 mmol, 1.0 equiv),α-oxocarboxylic acids (60.0 mg, 0.4 mmol, 2.0 equiv) and K2S2O8 (108.1 mg, 0.4 mmol, 2.0 equiv) under a gentle stream of argon. After Diglyme (1 mL) was added to the vial by a syringe. The vessel was heated in an oil bath at 80 °C for 20 h followed by cooling. The contents were subjected to flash chromatography to give the corresponding product (89percent) as a pale yellow oil. The purified material was dried under an oil-pump vacuum.

76%

With dipotassium peroxodisulfate; palladium diacetate in 1,4-dioxane; acetic acid

T=80°C; 12 h; regioselective reaction; Hide Experimental Procedure

Yao, Jia-Ping; Wang, Guan-Wu

Tetrahedron Letters, 2016 , vol. 57, # 15 p. 1687 - 1690 Title/Abstract Full Text View citing articles Show Details

2) General Procedures

147

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Rx-ID: 41975313

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87%

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With dipotassium peroxodisulfate; palladium(II) trifluoroacetate in diethylene glycol dimethyl ether

T=80°C; 20 h; Inert atmosphere; Catalytic behavior; regioselective reaction; Hide Experimental Procedure

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Zhang, Liang; Wang, Zhe; Guo, Peiyu; Sun, Wei; Li, Ya-Min; Sun, Meng; Hua, Chengwen

Tetrahedron Letters, 2016 , vol. 57, # 23 p. 2511 - 2514 Title/Abstract Full Text View citing articles Show Details

General catalytic procedure forortho-acylation of N-nitrosoaniline with α-keto acids.

86%

With ammonium peroxydisulfate; palladium diacetate in diethylene glycol dimethyl ether

T=20°C; 18 h; Sealed tube;

Wu, Yinuo; Sun, Lei; Chen, Yunyun; Zhou, Qian; Huang, Jia-Wu; Miao, Hui; Luo, Hai-Bin

Journal of Organic Chemistry, 2016 , vol. 81, # 3 p. 1244 - 1250 Title/Abstract Full Text View citing articles Show Details

81%

With dipotassium peroxodisulfate; palladium diacetate in 1,4-dioxane; acetic acid

T=80°C; 12 h; Catalytic behavior; Reagent/catalystSolventTemperature; regioselective reaction; Hide Experimental Procedure

Yao, Jia-Ping; Wang, Guan-Wu

Tetrahedron Letters, 2016 , vol. 57, # 15 p. 1687 - 1690 Title/Abstract Full Text View citing articles Show Details

2) General Procedures

148

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Rx-ID: 43681510

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89%

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Stage #1: oxalyl dichloride; Benzoylformic acid in chloroform

T=20°C; 1 h; Stage #2: (R)-quinuclidin-3-ol in chloroform

T=0 - 20°C; 1 h; ConcentrationSolvent; Hide Experimental Procedure

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CHIESI FARMACEUTICI S.p.A.; RANCATI, Fabio; RIZZI, Andrea; CARZANIGA, Laura; LINNEY, Ian; KNIGHT, Chris; SCHMIDT, Wolfgang

Patent: US2016/235734 A1, 2016 ; Location in patent: Paragraph 0419; 0420; 0421 ; Title/Abstract Full Text Show Details

2:Step 2; (R)-Quinuclidin-3-yl 2-oxo-2-phenylacetate

benzoylformic acid (50.00 g, 0.33 mol) was dissolved in chloroform (400 mE) and oxalyl chloride (40.02mE, 0.47 mol) was added drop-wise at room temperature. The reaction mixture stirred for 1 hour and the solvent evaporated under reduced pressure. The residue was dissolved in chloroform (305 mE) and cooled to 00 C. A solution of 3-(R)- quinuclidinol (50.83 g, 0.40 mmol) in chloroform (200 mE) was added drop-wise. The reaction mixture was allowed warm to room temperature and stirred for 1 hour. The reaction mixture was cooled to 00 C. and quenched with 10percent aqueous potassium carbonate solution. The organic layer was separated and washed with water (2x), brine (3x) and dried over anhydrous magnesium sulfate. The filtrate was evaporated under reduced pressure to afford the title compound (77.2 g, 89percent).10421] ‘H NMR (400 MHz, DMSO-d5) ö 8.01-7.95 (m, 2H), 7.84-7.77 (m, 1H), 7.68-7.61 (m, 2H), 5.15-5.05 (m, 1H), 3.26 (dd, J=14.7, 8.2 Hz, 1H), 2.79-2.58 (m, 5H), 2.13-2.04 (m, 1H), 1.72-1.53 (m, 3H), 1.42-1.33 (m, 1H).

149

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Rx-ID: 44045671

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33%

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With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride in N,N-dimethylformamide

T=20°C; 1.5 h; Hide Experimental Procedure

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Shanghai De Novo Pharmatech Co., Ltd; Gao, Daxin

Patent: CN102952118 B, 2016 ; Location in patent: Paragraph 0233-0236 ; Title/Abstract Full Text Show Details

6:1-(4-{2-fluoro-5-[(4-oxo-3,4,5,6,7,8-hexahydrophthalazin-1-yl)methyl]benzoyl}piperazin-1-yl)-2-phenylethane-1,2-dione

A mixture of 4-(4-fluoro-3-(piperazine-1-carbonyl)benzyl)-5,6,7,8-tetrahydrophthalazin-1(2Η)-one (20 mg, 0.054 mmol), 2-oxo-2-phenylacetic acid(ll mg, 0.074 mmol) H0Bt (12 mg, 0.089 mmol) and EDCI (28 mg, 0.15 mmol) Was dissolved in DMF (3 ml). The reaction was stirred at room temperature for 1.5 h (monitored by TLC) The mixture was diluted with water (10 ml) The aqueous phase was extracted with ethyl acetate (15 ml of X 3) The combined organic phases were washed with saturated brine (15 ml) Dried over anhydrous sodium sulfate, filtered and the filtrate concentrated to give the crude product, And then purified by TLC preparative plate (DCM: M = O H = 20: 1) To give the desired product (8 mg, 33percent), As an off-white solid.

150

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Rx-ID: 44108584

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92.3%

in methanol

T=45 - 65°C; 5 h; Time; Hide Experimental Procedure

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Hengyang Teachers College; Jiang, Wujiu; Zhang, Fuxing; Tan, Yu Xing; Yu, Jiang Xi; Kuang, Dai Zhi; Feng, Yong Lan; Zhu, Xiaoming

Patent: CN105601663 A, 2016 ; Location in patent: Paragraph 0042; 0043; 0044; 0045; 0046; 0047; 0048 ; Title/Abstract Full Text Show Details

2:example 2

0.344 g (1.0 mmol) of diphenyltin dichloride, 0.152 g (1.0 mmol) of t-butyldimethylsilane,Salicylhydrazide,(1.05 mmol)Benzoylformic acidAnd 35mL solvent anhydrous methanol, the temperature 45 ~ 65 ° C under the conditions of reaction 5h, cooling, filtration, 20 ~ 35 ° C under the control of solvent evaporation crystallization, yellow transparent crystals, namely 2-carbonyl-2- Phenylacetic acid salicyloylhydrazone diphenyltin complex. Yield: 92.3percent

151

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Rx-ID: 1322462

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52%

With Xtalfluor-E® in tetrahydrofuran

T=0 - 20°C; 4 h; Inert atmosphereCooling with ice;

Orliac, Aurelie; Gomez Pardo, Domingo; Bombrun, Agnes; Cossy, Janine

Organic Letters, 2013 , vol. 15, # 4 p. 902 - 905 Title/Abstract Full Text View citing articles Show Details

(i) Py, 6,6-dioxo-5,7-diphenyl-6H-6λ6-thieno<3,4-b><1,4>dioxine-2,3-dione, (ii) /BRN= 741984/; Multistep reaction;

Steglich,W. et al.

Synthesis, 1978 , p. 622 - 624 Full Text View citing articles Show Details

Stage #1: Benzoylformic acid With thionyl chloride; triethylamine in dichloromethane

T=0°C; 0.333333 h; Inert atmosphere; Stage #2: Benzyl amine in dichloromethane

T=0 - 20°C; Inert atmosphere;

Mamillapalli, N. Chary; Sekar, Govindasamy

RSC Advances, 2014 , vol. 4, # 105 p. 61077 - 61085 Title/Abstract Full Text View citing articles Show Details

Hide Details

Stage #1: Benzoylformic acid With thionyl chloride; triethylamine in dichloromethane

T=0°C; 0.333333 h; Inert atmosphere; Stage #2: Benzyl amine in dichloromethane

T=0 - 20°C; Inert atmosphere;

Mamillapalli, N. Chary; Sekar, Govindasamy

Chemistry - A European Journal, 2015 , vol. 21, # 51 p. 18584 - 18588 Title/Abstract Full Text View citing articles Show Details

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152

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With titanium(IV) isopropylate; 1,2:5,6-di-O-isopropylidene-D-mannitol; lithium diisopropyl amide

multistep reaction, other α-keto aromatic acid: 4-CH3OC6H4COCOOH, 1.) toluene, benzene, heating; other reagents: (EtO)4Ti, (tBuO)4Ti, 2.) toluene, heating, 3.) toluene, ether, hexane, -50 -> -40 deg C, 1 h; other reagents: other lithium dialkyl amides; Product distribution;

Duan, Xin-Fang; Yin, Cheng-Lie

Synthetic Communications, 1997 , vol. 27, # 5 p. 825 - 828 Title/Abstract Full Text Show Details

With sodium tetrahydroborate; L-Tartaric acid in tetrahydrofuran

T=0°C; 67 h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

Yatagai, Masanobu; Ohnuki, Takashi

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990 , # 6 p. 1826 - 1828 Title/Abstract Full Text View citing articles Show Details

With buffered acetic acid; strychnidin-10-one; mercury

var. strychnine concentrations, other cathodic potentials (E): -1.10, -1.20, -1.30 V (SCE); object of study: optical yield; Product distribution;

Jubault, Michel

Journal of the Chemical Society, Chemical Communications, 1980 , # 20 p. 953 - 954 Title/Abstract Full Text View citing articles Show Details

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With diisopinocampheylborane in tetrahydrofuran

T=20°C; 10 h; Title compound not separated from byproducts.;

Veeraraghavan Ramachandran; Brown, Herbert C.; Pitre, Sangeeta

Organic Letters, 2001 , vol. 3, # 1 p. 17 - 18 Title/Abstract Full Text View citing articles Show Details

With [iridium(dihydride)(chloride)((3,5-(tBu)2-C6H3)2P)(C17H10)NHCHC5H3N(CH3)]; potassium tertbutylate; hydrogen in butan-1-ol

T=25 - 30°C; P=11400.8 Torr; 2 h; Autoclave; Catalytic behavior; Reagent/catalystSolvent; enantioselective reaction;

Yan, Pu-Cha; Xie, Jian-Hua; Zhang, Xiang-Dong; Chen, Kang; Li, Yuan-Qiang; Zhou, Qi-Lin; Che, Da-Qing

Chemical Communications, 2014 , vol. 50, # 100 p. 15987 - 15990 Title/Abstract Full Text View citing articles Show Details

With tetraethylammonium iodide; water; Cinchonidin in acetonitrile

Electrochemical reaction; Overall yield = 36 percentChromat.; enantioselective reaction; Hide Experimental Procedure

Yang, Heng-Pan; Wang, Huan; Lu, Jia-Xing

Electrochemistry Communications, 2015 , vol. 55, p. 18 - 21 Title/Abstract Full Text View citing articles Show Details

2.2. General procedure

General procedure: The synthesis of Cu (Pt) NPs was performed as follows. 5 g of CuSO4*5H2O (2.07 g H2PtCl6*6H2O) was dissolved in 100 mL deionized water. 8 mL of ethylene glycol was then added into the solution. After 10 min of stirring, 50 mL of hydrazine hydrate solution (10percent) was slowly added. The mixture was then stirred at 25 °C for 4 h. Cu (Pt) was precipitated immediately. The precipitate was filtered, washed with 10 mL water and 10 mL anhydrous ethanol for 4 times each, and dried for 12 h under vacuum. The electrohydrogenation procedure is as follows. Cu NP powder was pressed into a coin and used as a cathode. Typical galvanostatic electrohydrogenation was conducted in a mixture of 50mM substrate, certain concentration of alkaloid and 0.1M tetraethylammonium iodide (TEAI) in a 20mL co-solvent (MeCN/H2O=9/1) in an undivided glass cell with a Cu NP cathode and sacrificial magnesium (Mg) anode.

With chiral spiro phosphine Iridium complex in ethanol

T=20°C; P=11400.8 Torr; 10 h; SolventReagent/catalyst; Hide Experimental Procedure

Zhejiang Jiuzhou Pharmaceutical Co., Ltd.; Yan, Pucha; Che, Daqing; Lin, Yuanqiang; Zhang, Xiangdong; Chen, Kang; Yan, Yongliang

Patent: CN105481677 A, 2016 ; Location in patent: Paragraph 0033; 0037 ; Title/Abstract Full Text Show Details

With tetraethylammonium iodide; water in acetonitrile

T=20°C; Electrochemical reaction; Overall yield = 87 percent; Optical yield = 54 percent ee; enantioselective reaction; Hide Experimental Procedure

Yang, Heng-Pan; Fen, Qiu; Wang, Huan; Lu, Jia-Xing

Electrochemistry Communications, 2016 , vol. 71, p. 38 - 42 Title/Abstract Full Text View citing articles Show Details

General procedure: Typical electrochemical hydrogenation was conducted in a mixtureof 50 mM substrate, 0.1 M tetraethylammonium iodide (TEAI) in a20 mL co-solvent (MeCN/H2O = 9/1) in an undivided glass cell withan alkaloidCu cathode and sacrificialmagnesium(Mg) anode. The currentdensitywas 10mAcm−2 and the chargewas 300 C. The electrolytewas bubbled with high purity N2 throughout the electrolysis. All theprocedure was performed at room temperature.

153

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Rx-ID: 24349085

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63%

With toluene-4-sulfonic acid in N,N-dimethyl-formamide

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Development Center for Biotechnology

Patent: US6071913 A1, 2000 ; Title/Abstract Full Text Show Details

9:Preparation of 3-butyl-6-phenyl-1,2,4-triazin-5-one

Example 9 Preparation of 3-butyl-6-phenyl-1,2,4-triazin-5-one Valeroyl N-formyl hydrazidine (500 mg, 3.5 mmole) was mixed with p-toluenesulphonic acid (865 mg, 4.55 mmole) then dissolved in 4 ml DMF, and the mixture was stirred at room temperature for 1 hour. The benzoylformic acid (0.59 g, 3.85 mmole) dissolved in DMF (3 ml) was slowly added. The mixture was stirred for 4 hours, and heated to reflux temperature overnight. The solution was concentrated, and the product was obtained as white powder (0.50 g, 63percent) after purified by column chromatography. 1 H NMR (DMSO-d6, δ) 8.08-8.02 (m, 2H), 7.40-7.31 (m, 3H), 2.59 (t, 2H, J=7.6 Hz), 1.79-1.68 (m, 2H), 1.43-1.25 (m, 2H), 0.87 (t,

3H, J=7.2 Hz).

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154

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Rx-ID: 27832038

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A: 10% B: 80%

Stage #1: With sulfuric acid in water

T=60°C; 1 h; Stage #2: With sodium hydroxide in water

Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 23 p. 7070 - 7084 Title/Abstract Full Text View citing articles Show Details

Hide Experimental Procedure

5.1.11. General procedure for preparation of pyrido[2,3-g]quinoxalines 3e-f, 4g-j and 5k-o

With sulfuric acid in water; N,N-dimethyl-formamide

T=60°C; 1 h; Hide Experimental Procedure

CARTA, Antonio; LA COLLA, Paolo; LODDO, Roberta; PAGLIETTI, Giuseppe

Patent: WO2008/81266 A1, 2008 ; Location in patent: Page/Page column 10-11 ; Title/Abstract Full Text Show Details

A mixture of g 0.4 (2.07 mmoles) of 6,7-diamino-8-chloroquinoline, prepared according to the procedure given in Sanna et al., [Paolo Sanna, Antonio Carta, and Giuseppe Paglietti, Synthesis of triazolo[4,5-g]quinolines and pyrido[2,3- gjquinoxalines derived from 6,7diammoquinolmes. Heterocycles, 53, 423-432 <n="12"/>(2000)] and g 0.35 (2.33 mmoles) of benzoylformic acid, in 10percent sulphuric acid aqueous solution DMF (10 mL) was stirred at 60 0C for 1 h. On cooling to room temperature the resulting precipitate was filtered off, washed with water and crystallised by ethanol affording g 0.80 of 5-chloro-3-phenyl-l,2-dihydropyrido[2,3- g]quinoxalin-2-one, m.p. >300 0C; 1H NMR (DMSO-d6): δ 12.76 (IH, s), 8.97 (IH, d, J = 3.6 Hz), 8.45 (3H, m), 7.60 (5H, m), and g 0.03 of 5-chloro-2-phenyl-3,4dihydropyrido[2,3-g]quinoxarm-3-one, m.p. >300 °C; 1H NMR (DMSOd6): δ 12.51 (IH, s), 9.10 (IH, d, J= 3.8 Hz), 8.65 (2H, m), 8.28 (2H, m), 7.64 (3H, s).

155

Rx-ID: 31146105

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25%

Stage #1: C25H28N6O2; α-ketophenylacetic acid With N-ethyl-N,N-diisopropylamine; HATU in N,N-dimethylformamide

T=20°C; 16 h; Stage #2: trifluoroacetic acid Hide Experimental Procedure

BRISTOL-MYERS SQUIBB COMPANY; LOPEZ, Omar D.; ST. LAURENT, Denis R.; GOODRICH, Jason; ROMINE, Jeffrey Lee; SERRANO-WU, Michael; YANG, Fukang; KAKARLA, Ramesh; YANG, Xuejie; QIU, Yuping; SNYDER, Lawrence B.

Patent: WO2011/82077 A1, 2011 ; Location in patent: Page/Page column 314 ; Title/Abstract Full Text Show Details

JG-31:

HATU (45 mg, 0.1 19mmol)) was added in one portion to a stirred solution of OL-31b (30 mg, 0.054mmol), diisopropylethylamine (0.060 ml, 0.324 mmol) and benzoyl formic acid (18 mg, 0.1 19mmol) in anhydrous dimethylformamide (1.5mL) at room temperature. The mixture was stirred for 16h. Solvents were removed in vacuo and residue was purified by preparatory HPLC on C18- reverse phase to afford JG-31 as a trifluoroacetic acid salt, 1 1.3 mg ( 25percent yield). 1H NMR (500 MHz, DMSO-de) δ ppm 10.40 (2 H, br. s.), 8.06 (1 H, s), 8.05 (2 H, d, J=1.2 Hz), 7.87 - 7.94 (1 H, m), 7.76 - 7.85 (4 H, m), 7.70 - 7.75 (3 H, m), 7.63 - 7.69 (4 H, m), 7.53 (1 H, t, J=7.8 Hz), 7.36 (1 H, d, J=8.5 Hz), 7.09 (1 H, s), 4.58 - 4.71 (2 H, m), 3.69 (2 H, br. s.), 3.35 - 3.55 (4 H, m), 2.28 - 2.48 (2 H, m), 1.87 - 1.98 (6 H, m); LCMS (Cond. JG4 ) Rt= 2.20 min, Anal. Calc. for [M+H]+ C4iH37 606 :709.8; found 709.3.

156

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Rx-ID: 33423516

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69%

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With RbOH in water; 1,2-dichloro-ethane

2 h; Inert atmosphereReflux; Hide Experimental Procedure

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E.I. DU PONT DE NEMOURS AND COMPANY

Patent: EP2016154 B1, 2012 ; Location in patent: Page/Page column 9 ; Title/Abstract Full Text Show Details

1.0 g (0.0006 mol) of Iridium, di-μ-chlorotetrakis[4,6-bis(trifluromethyl)-2-(4-methyl-2-pyridinyl-κN)phenyl-κC]di-, 0.35 g (0.0023 mol) of benzoylformic acid, 0.60 g (0.0059 mol) of rubidium hydroxide in 5 ml of water, and 40 ml of 1,2-dichloroetane were refluxed for 2 hours under argon atmosphere. The precipitate was filtered off, washed with 20 ml of water and recrystallized from DMSO. Yield of iridium, di-μ-hydroxytetrakis[4,6-bis(trifluromethyl)-2-(4-methyl-2-pyridinyl-κN)phenyl-κC]di-, was 0.67 g (69percent) as yellow solid with no m.p. until 200°C. 1H NMR (CD2Cl2) 2.60 (br, 6H, Me), 6.10-8.50 (m, 15H, arom-H). 19F NMR (CD2Cl2) - 58.97 (br, 6F, CF3), -63.11 (br, 6F, CF3). Anal. Calcd. for C56H34F24Ir2N4O2 (Mol. Wt.: 1635.30): C, 41.13; H, 2.10; N, 3.43. Found: C, 41.20; H, 2.10; N, 3.49. The structure was proven by X-ray analysis.

157

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Rx-ID: 35820818

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85%

With palladium(II) trifluoroacetate; silver carbonate in DME

T=165°C; 24 h; Sealed tube; chemoselective reaction;

Miao, Jinmin; Ge, Haibo

Organic Letters, 2013 , vol. 15, # 12 p. 2930 - 2933 Title/Abstract Full Text View citing articles Show Details

With palladium(II) trifluoroacetate; silver carbonate in DME

T=150 - 165°C; regioselective reaction;

Pan, Shulei; Zhou, Bo; Zhang, Yanghui; Shao, Changdong; Shi, Guangfa

Synlett, 2016 , vol. 27, # 2 art. no. ST-2015-W0600-L, p. 277 - 281

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(20) Synthesis of para-Benzoylated Arenes

General procedure: A mixture of m-toluic acid (27.2 mg, 0.20 mmol), benzoylformicacid (90.1 mg, 0.60 mmol), Pd(TFA)2 (6.6 mg, 0.020 mmol), andAg2CO3 (165.5 mg, 0.60 mmol) in DME (2 mL) was heated at150–165 °C for 24–48 h. After cooling down to r.t., the reactionmixture was diluted by addition of EtOAc (10 mL) and then filteredthrough a pad of Celite. The filtrate was concentrated invacuo to afford 2-benzoylbenzoic acid derivatives. A mixture ofthe crude product, Cu2O (1.4 mg, 0.010 mmol), and 1,10-phenanthroline (3.6 mg, 0.020 mmol) in a solution of NMP (1.5mL) and quinoline (0.5 mL) was heated under an atmosphere ofN2 at 170 °C for 24 h. The reaction mixture was quenched byaddition of 0.2 M aq HCl (10 mL), diluted with EtOAc (10 mL),and then filtered through a pad of Celite. The filtrate waswashed with brine (10 mL), dried over Na2SO4, and concentratedin vacuo. The residue was purified by silica gel preparativeTLC to give phenyl(p-tolyl)methanone.

158

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Rx-ID: 36217035

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18%

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With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride in dichloromethane

T=20°C; 5 h; Cooling with ice; Hide Experimental Procedure

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Mahaveer; Kulkarni; Radakrishna; Chandrashekar; Achaiah

Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013 , vol. 52, # 6 p. 818 - 823 Title/Abstract Full Text View citing articles Show Details

Coupling of amines and acids 6a-i (Scheme I)

159

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Rx-ID: 40545759

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91%

With dipotassium peroxodisulfate in water; acetonitrile

T=50°C; 24 h; Inert atmosphereSealed tube;

Wang, Hua; Guo, Li-Na; Wang, Shun; Duan, Xin-Hua

Organic Letters, 2015 , vol. 17, # 12 p. 3054 - 3057 Title/Abstract Full Text View citing articles Show Details

72%

With dipotassium peroxodisulfate in water; acetonitrile

T=50°C; 12 h; Inert atmosphereSchlenk techniqueSealed tube;

Wang, Peng-Fei; Feng, Yi-Si; Cheng, Zhi-Fei; Wu, Qiu-Min; Wang, Guang-Yu; Liu, Liang-Liang; Dai, Jian-Jun; Xu, Jun; Xu, HuaJian

Journal of Organic Chemistry, 2015 , vol. 80, # 18 p. 9314 - 9320 Title/Abstract Full Text View citing articles Show Details

160

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Rx-ID: 41406491

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72%

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With Potassium peroxomonosulfate

T=65°C; 40 h; Hide Experimental Procedure

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Padala, Anil K.; Saikam, Varma; Ali, Asif; Ahmed, Qazi Naveed

Tetrahedron, 2015 , vol. 71, # 50 p. 9388 - 9395 Title/Abstract Full Text View citing articles Show Details

4.3 General procedure for preparation of esters (RCO2R′) 5 from 2-oxoacids (RCOCO2H) 3/2-oxoaldehydes (RCOCHO) 3 &/2-oxoesters (RCOCO2R″) 4

161

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Rx-ID: 41975316

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83%

With ammonium peroxydisulfate; palladium diacetate in diethylene glycol dimethyl ether

T=20°C; 18 h; Sealed tube;

Wu, Yinuo; Sun, Lei; Chen, Yunyun; Zhou, Qian; Huang, Jia-Wu; Miao, Hui; Luo, Hai-Bin

Journal of Organic Chemistry, 2016 , vol. 81, # 3 p. 1244 - 1250 Title/Abstract Full Text View citing articles Show Details

75%

With dipotassium peroxodisulfate; palladium(II) trifluoroacetate in diethylene glycol dimethyl ether

T=80°C; 20 h; Inert atmosphere; Catalytic behavior; regioselective reaction; Hide Experimental Procedure

Zhang, Liang; Wang, Zhe; Guo, Peiyu; Sun, Wei; Li, Ya-Min; Sun, Meng; Hua, Chengwen

Tetrahedron Letters, 2016 , vol. 57, # 23 p. 2511 - 2514 Title/Abstract Full Text View citing articles Show Details

General catalytic procedure forortho-acylation of N-nitrosoaniline with α-keto acids.

51%

With dipotassium peroxodisulfate; palladium diacetate in 1,4-dioxane; acetic acid

T=80°C; 12 h; regioselective reaction; Hide Experimental Procedure

Yao, Jia-Ping; Wang, Guan-Wu

Tetrahedron Letters, 2016 , vol. 57, # 15 p. 1687 - 1690 Title/Abstract Full Text View citing articles Show Details

2) General Procedures

162

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Rx-ID: 41975317

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86%

With ammonium peroxydisulfate; palladium diacetate in diethylene glycol dimethyl ether

T=20°C; 18 h; Sealed tube;

Wu, Yinuo; Sun, Lei; Chen, Yunyun; Zhou, Qian; Huang, Jia-Wu; Miao, Hui; Luo, Hai-Bin

Journal of Organic Chemistry, 2016 , vol. 81, # 3 p. 1244 - 1250 Title/Abstract Full Text View citing articles Show Details

79%

With dipotassium peroxodisulfate; palladium(II) trifluoroacetate in diethylene glycol dimethyl ether

T=80°C; 20 h; Inert atmosphere; Catalytic behavior; regioselective reaction; Hide Experimental Procedure

Zhang, Liang; Wang, Zhe; Guo, Peiyu; Sun, Wei; Li, Ya-Min; Sun, Meng; Hua, Chengwen

Tetrahedron Letters, 2016 , vol. 57, # 23 p. 2511 - 2514 Title/Abstract Full Text View citing articles Show Details

General catalytic procedure forortho-acylation of N-nitrosoaniline with α-keto acids.

50%

With dipotassium peroxodisulfate; palladium diacetate in 1,4-dioxane; acetic acid

T=80°C; 12 h; regioselective reaction; Hide Experimental Procedure

Yao, Jia-Ping; Wang, Guan-Wu

Tetrahedron Letters, 2016 , vol. 57, # 15 p. 1687 - 1690 Title/Abstract Full Text View citing articles Show Details

2) General Procedures

163

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Rx-ID: 42792799

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18%

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With pyridine; methanesulfonyl chloride in tetrahydrofuran

T=0 - 20°C; 0.416667 h; Hide Experimental Procedure

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Ota, Eisuke; Mikame, Yu; Hirai, Go; Nishiyama, Shigeru; Sodeoka, Mikiko

Synlett, 2016 , vol. 27, # 7 p. 1128 - 1132 Title/Abstract Full Text View citing articles Show Details

Synthesis of 13f (Typical procedure for synthesis of 13b, 13c, 13d, 13e, and 13f)

General procedure: To a solution of 3-methyl-2-oxo-butanoic acid sodium salt (1.03 g, 7.47 mmol) in THF (9.8 ml)were added α,α-dimethoxy benzenemethanol (2.05 g, 15.0 mmol) and pyridine (1.55 ml, 18.7 mmol).The mixture was cooled to 0 °C, and methanesulfonyl chloride (700 μL, 8.97 mmol) was added. The reaction mixture was stirred for 25 min at room temperature before quenching with distilled water at 0 °C. The resulting mixture was extracted with diethylether twice. The combined organic layers were washed with brine, dried over MgSO4, and concentrated in vacuo. Further purification was carriedout by silica gel column chromatography to give 13f (699.7 mg, 40percent) as a colorless oil.

164

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Rx-ID: 728409

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With diethyl ether

McKenzie; Ritchie

Chemische Berichte, 1937 , vol. 70, p. 23,31 Full Text Show Details

Hanney, Barbara; Kim, Yuntae; Krout, Michael R.; Meissner, Robert S.; Mitchell, Helen J.; Musselman, Jeffrey; Perkins, James J.; Wang, Jiabing

Patent: US2005/277681 A1, 2005 ; Location in patent: Page/Page column 32-33 ;

Stage #1: in tetrahydrofuran

T=20°C; 5 h; Stage #2: With hydrochlorid acid in tetrahydrofuran; water

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Title/Abstract Full Text Show Details

2.1:

(2R or 2S)-N-(2-fluoro-5-(trifluoromethyl)benzyl)-2-hydroxy-2-phenylbutanamide (2-1) A solution of 2-oxo-2-phenylacetic acid (10 g, 66.6 mmol) (Acros Organics B.V.B.A., Belgium) in tetrahydrofuran (THF, 200 mL) was treated at room temperature with ethylmagnesium bromide (2.5 M, 80 mL, 200 mmol). The reaction mixture was stirred for 5 h, partitioned between ethyl acetate and 1N-HCl. The organic layer was separated, dried (MgSO4) and concentrated in vacuo to afford 2-hydroxy-2-phenylbutanoic acid.

165

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Rx-ID: 728430

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99%

With chlorobenzene in methanol

T=40°C; 5 h; Sealed tubeGreen chemistry; chemoselective reaction;

Volkov, Alexey; Gustafson, Karl P. J.; Tai, Cheuk-Wai; Verho, Oscar; Bäckvall, Jan-E.; Adolfsson, Hans

Angewandte Chemie - International Edition, 2015 , vol. 54, # 17 p. 5122 - 5126 Angew. Chem., 2015 , vol. 54, # 17 p. 5211 - 5215,5 Title/Abstract Full Text View citing articles Show Details

94.3%

With orthophosphorus acid; methanesulfonic acid; sodium iodide in water

T=95°C; 48 h; Inert atmosphere;

Milne, Jacqueline E.; Storz, Thomas; Colyer, John T.; Thiel, Oliver R.; Dilmeghani Seran, Mina; Larsen, Robert D.; Murry, Jerry A.

Journal of Organic Chemistry, 2011 , vol. 76, # 22 p. 9519 - 9524 Title/Abstract Full Text View citing articles Show Details

With hydrazine hydrate

anschliessend Erhitzen mit KOH;

Lock

Oest. Chemiker-Ztg., 1950 , vol. 51, p. 77 Full Text Show Details

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With phosphorus; hydrogen iodide

Claisen

T=160°C;

Chemische Berichte, 1877 , vol. 10, p. 847 Full Text Show Details

166

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Rx-ID: 2918710

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79%

With sodium hydroxide in water

T=90°C; 0.5 h;

Arndt, Friedrich; Franke, Wilfried; Klose, Walter; Lorenz, Joerg; Schwarz, Katica

Liebigs Annalen der Chemie, 1984 , # 7 p. 1302 - 1307 Title/Abstract Full Text Show Details

Stage #1: With hydrogenchloride in water

2.5 h; Heating / reflux; Stage #2: With sodium hydroxide in water

pH=~ 14; 4 h; Heating / reflux; Stage #3: With acetic acid in water

T=0°C; pH=4; Hide Experimental Procedure

AVENTIS PHARMA S.A.

Patent: US2008/96891 A1, 2008 ; Location in patent: Page/Page column 5 ; Title/Abstract Full Text Show Details

3.1:

Add 0.88 cm3 of 12N hydrochloric acid to a suspension of 10 g of oxo-phenyl-acetic acid and 7 g of thiosemicarbazide in 150 cm3 of water and heat the mixture with stirring for 2.5 h with reflux of the reaction mixture. After cooling the mixture in a bath of ice water, collect the suspended solid by filtration, rinse with water and dry in air. After taking up the pale yellow solid obtained (15.5 g) in 150 cm3 of water and adjusting the mixture to a pH close to 14 with 1N sodium hydroxide, heat the mixture for 4 h with stirring and with reflux of the reaction mixture, cool it on an ice bath, and adjust the pH to 4 by adding acetic acid. The resulting precipitate is collected by filtration, rinsed with water and dried on a screen for 2 days to give 11.3 g of 3-mercapto-6-phenyl-4H-1,2,4-triazin-5-one in the form of a pale yellow solid. Mass spectrum (IE): m/z=205 (M+., base peak), m/z=118 ((M-C2HNOS)+), m/z=104 (C7H6N+).

167

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Rx-ID: 3393151

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89%

With trifluoroacetic acid in isopropyl alcohol

T=70°C; 18 h;

Yan, Shaoxi; Ye, Leping; Liu, Miaochang; Chen, Jiuxi; Ding, Jinchang; Gao, Wenxia; Huang, Xiaobo; Wu, Huayue

RSC Advances, 2014 , vol. 4, # 32 p. 16705 - 16709 Title/Abstract Full Text View citing articles Show Details

46%

With Oxonereg; in diethylene glycol dimethyl ether; dimethyl sulfoxide

T=120°C; 12 h;

Wang, Hua; Yang, Hua; Li, Yiping; Duan, Xin-Hua

RSC Advances, 2014 , vol. 4, # 17 p. 8720 - 8722 Title/Abstract Full Text View citing articles Show Details

Tauer, Erich; Grellmann, Karl-Heinz

Chemische Berichte, 1986 , vol. 119, # 1 p. 215 - 228

Title/Abstract Full Text Show Details

168

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Rx-ID: 4784251

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85%

2 h; Heating;

Hu, Shengkui; Neckers, Douglas C.

Journal of Organic Chemistry, 1997 , vol. 62, # 20 p. 6820 - 6826 Title/Abstract Full Text View citing articles Show Details

81%

With toluene-4-sulfonic acid in benzene

16 h; Heating;

Heaney, Frances; O'Mahony, Colm

Journal of the Chemical Society - Perkin Transactions 1, 1998 , # 2 p. 341 - 349 Title/Abstract Full Text View citing articles Show Details

80%

Stage #1: With dmap in dichloromethane

T=0°C; 0.25 h; Inert atmosphere; Stage #2: With dicyclohexyl-carbodiimide in dichloromethane

6 h; Inert atmosphere;

Rodriguez, Nuria; Manjolinho, Filipe; Gruenberg, Matthias F.; Goossen, Lukas J.

Chemistry - A European Journal, 2011 , vol. 17, # 49 p. 13688 - 13691 Title/Abstract Full Text View citing articles Show Details

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48%

With dmap; dicyclohexyl-carbodiimide in dichloromethane

T=0 - 20°C; 18 h;

Bartrum, Hannah E.; Blakemore, David C.; Moody, Christopher J.; Hayes, Christopher J.

Chemistry - A European Journal, 2011 , vol. 17, # 35 p. 9586 - 9589 Title/Abstract Full Text View citing articles Show Details

Stage #1: With dmap in dichloromethane

T=0°C; 0.25 h; Stage #2: With dicyclohexyl-carbodiimide in dichloromethane

Chen, Zi-Sheng; Duan, Xin-Hua; Zhou, Ping-Xin; Ali, Shaukat; Luo, Jian-Yi; Liang, Yong-Min

Angewandte Chemie - International Edition, 2012 , vol. 51, # 6 p. 1370 - 1374 Title/Abstract Full Text View citing articles Show Details

169

Howard, Brett E.; Woerpel

Organic Letters, 2007 , vol. 9, # 22 p. 4651 - 4653 Title/Abstract Full Text View citing articles Show Details

With dmap; dicyclohexyl-carbodiimide in dichloromethane

T=0 - 20°C; 16.0833 h; Inert atmosphere;

Nicolle, Simon M.; Hayes, Christopher J.; Moody, Christopher J.

Chemistry - A European Journal, 2015 , vol. 21, # 12 p. 4576 - 4579 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 23991806

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88%

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Neurocrine Biosciences, Inc.

Patent: US2003/114455 A1, 2003 ;

in ethanol; water

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Title/Abstract Full Text Show Details

1.A:Step 1A

Step 1A 6-Phenyl-1,2,4-triazine-3,5-(2H,4H)-dione To benzoylformic acid (10.0 g, 66.6 mmol) in water (30 mL) was added semicarbazide hydrochloride (6.66 g, 5.97 mmol) in water/ethanol (7:2, 180 mL). A thick white precipitate immediately formed, and vigorous stirring was continued for 16 hours. The mixture was filtered, and the precipitate was washed with water (2*5 mL), and dried in vacuo for 2 days to give the crude benzoylformic acid semicarbazone (12.2 g, 88percent) as a white powder. [Dufresne, J. C.; Fleury, M. B. Bull. Soc. Chim. Fr. 1972, 2541.]

El-Brollosy, Nasser R.

Monatshefte fur Chemie, 2008 , vol. 139, # 12 p. 1483 - 1490 Title/Abstract Full Text View citing articles Show Details

in water

170

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Rx-ID: 25046993

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90%

With hydrogenchloride

Hide Experimental Procedure

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Kyowa Gas Chemical Industry Co. Ltd.

Patent: US4259489 A1, 1981 ; Title/Abstract Full Text Show Details

5.1:(1)

(1) Synthesis of 2,3-dicyano-5-hydroxy-6-phenylpyrazine Diaminomaleonitrile (5.40 g; 0.05 mole) and 7.50 g (0.05 mole) of benzoylformic acid were put into 50 ml of a 2 N aqueous solution of hydrochloric acid. The mixture was stirred at 20° to 30° C. for 30 minutes, and further stirred at 70° to 80° C. for 2 hours. The mixture was then cooled to room temperature. The precipitate formed was collected by filtration, washed thrice with 40 ml of water, and dried under reduced pressure to afford 10.0 g (yield 90percent) of 2,3-dicyano-5-hydroxy-6-phenylpyrazine. Melting point: 221°-223° C. (decomp.). Elemental analysis for C12 H6 N4 O: Calcd. C 64.86, H 2.72, N 25.21; Found C 65.02, H 2.54, N 25.20. IR (KBr) cm-1 νOH 2800-2500; νCN 2240.

171

in water

T=20°C;

Morkved

Chemistry of Heterocyclic Compounds, 2007 , vol. 43, # 9 p. 1197 - 1201 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 28030780

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90%

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With acetic anhydride

3 h; Heating / reflux; Hide Experimental Procedure

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UNIVERSITY-INDUSTRY COOPERATION GROUP OF KYUNG HEE UNIVERSITY

Patent: WO2008/140251 A2, 2008 ; Location in patent: Page/Page column 7 ; Title/Abstract Full Text Show Details

Example 1: Preparation of 3-benzor[1,3]dioxol-5-yl-4-phenylfuran-2.5dione (MCR-3004). Benzoylformic acid (1.67 g) and 3,4-(methylenedioxy)phenylacetic acid (2 g) were dissolved in acetic anhydride (20 ml) and refluxed for 3 hours. After the reaction was completed, the reaction mixture was allowed to cool to room temperature and treated with excessive water. Then, the reaction mixture was neutralized with a saturated NaHCO aqueous solution, extracted with ethyl acetate three times, and washed with a saline solution. The organic phase was dried with anhydrous magnesium sulfate (MgSO ) and distilled under reduced pressure. The resulting residue was recrystallized4 with ethanol and methanol to give the target compound as a yellow solid (2.93 g, 90 percent). [65] 1H NMR(430 MHz, DMS0-d6) δ 7.507.44(5H, m, Ph), 7.06-7.00(2H, m, PhOCH6 2O), 6.89(1H, m, PhOCH O), 6.10(2H, s, PhOCH. O)[66] 13C NMR (IOO MHz, DMS0-d6 ) δ 165.6, 149.9, l47.9, 138.4, 137.2, 13Q9, 129.8,129.3, 128.2, 125.3, 121.4, 109.5, 109.3, 102.3.

With acetic anhydride

Reflux;

Moon, Jong Taik; Jeon, Ji Young; Park, Hang Ah; Noh, Young-Soo; Lee, Kyung-Tae; Kim, Jungahn; Choo, Dong Joon; Lee, Jae Yeol

Bioorganic and Medicinal Chemistry Letters, 2010 , vol. 20, # 2 p. 734 - 737 Title/Abstract Full Text View citing articles Show Details

172

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Rx-ID: 29691240

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81%

With dipotassium peroxodisulfate; bis(benzonitrile)palladium(II) dichloride; silver(l) oxide in 1,4dioxane; acetic acid; dimethyl sulfoxide

T=120°C; 12 h;

Li, Mingzong; Ge, Haibo

Organic Letters, 2010 , vol. 12, # 15 p. 3464 - 3467 Title/Abstract Full Text View citing articles Show Details

11%

With tert -butyl hydrogen peroxide; palladium dichloride; 2-dicyclohexylphosphino-2’,4’,6’triisopropylbiphenyl in chlorobenzene

T=130°C; 8 h;

Zhang, Qian; Wang, Yang; Yang, Tingting; Li, Li; Li, Dong

Tetrahedron Letters, 2016 , vol. 57, # 1 p. 90 - 94 Title/Abstract Full Text View citing articles Show Details

173

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Rx-ID: 29764927

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84%

With ammonium peroxydisulfate; palladium(II) trifluoroacetate in diethylene glycol dimethyl ether

T=20°C;

Fang, Ping; Li, Mingzong; Ge, Haibo

Journal of the American Chemical Society, 2010 , vol. 132, # 34 p. 11898 - 11899 Title/Abstract Full Text View citing articles Show Details

79%

With oxygen; palladium diacetate; eosin y in chlorobenzene

T=20°C; 15 h; Irradiation;

Zhou, Chao; Li, Pinhua; Zhu, Xianjin; Wang, Lei

Organic Letters, 2015 , vol. 17, # 24 p. 6198 - 6201 Title/Abstract Full Text View citing articles Show Details

174

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Rx-ID: 29764939

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90%

With ammonium peroxydisulfate; palladium(II) trifluoroacetate in diethylene glycol dimethyl ether

T=20°C; 12 h;

Fang, Ping; Li, Mingzong; Ge, Haibo

Journal of the American Chemical Society, 2010 , vol. 132, # 34 p. 11898 - 11899 Title/Abstract Full Text View citing articles Show Details

80%

With oxygen; palladium diacetate; eosin y in chlorobenzene

T=20°C; 15 h; Irradiation; Reagent/catalystSolventWavelength;

Zhou, Chao; Li, Pinhua; Zhu, Xianjin; Wang, Lei

Organic Letters, 2015 , vol. 17, # 24 p. 6198 - 6201 Title/Abstract Full Text View citing articles Show Details

175

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Rx-ID: 29764941

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77%

With oxygen; palladium diacetate; eosin y in chlorobenzene

T=20°C; 15 h; Irradiation;

Zhou, Chao; Li, Pinhua; Zhu, Xianjin; Wang, Lei

Organic Letters, 2015 , vol. 17, # 24 p. 6198 - 6201 Title/Abstract Full Text View citing articles Show Details

76%

With ammonium peroxydisulfate; palladium(II) trifluoroacetate in diethylene glycol dimethyl ether

T=20°C;

Fang, Ping; Li, Mingzong; Ge, Haibo

Journal of the American Chemical Society, 2010 , vol. 132, # 34 p. 11898 - 11899 Title/Abstract Full Text View citing articles Show Details

176

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Rx-ID: 29886743

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75.3%

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride in N,N-dimethylformamide

T=20°C; 12 h; Inert atmosphere;

Hirsch-Weil, Dimitri; Abboud, Khalil A.; Hong, Sukwon

Chemical Communications, 2010 , vol. 46, # 40 p. 7525 - 7527 Title/Abstract Full Text View citing articles Show Details

75%

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride

T=20°C; 12 h; Inert atmosphere;

Rodig, Michael J.; Seo, Hwimin; Hirsch-Weil, Dimitri; Abboud, Khalil A.; Hong, Sukwon

Tetrahedron Asymmetry, 2011 , vol. 22, # 10 p. 1097 - 1102 Title/Abstract Full Text View citing articles Show Details

177

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Rx-ID: 33314211

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With N-ethyl-N,N-diisopropylamine; HATU in N,N-dimethyl-formamide

T=20°C; 96 h; Hide Experimental Procedure

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SHANGHAI DE NOVO PHARMATECH CO LTD.; GAO, Daxin

Patent: WO2012/71684 A1, 2012 ; Location in patent: Page/Page column 27 ; Title/Abstract Full Text Show Details

Example 41 -(4-(2-fluoro-5-((4-oxo-3,4-dihydrophthalazin-l -yl) methyl) benzoyl) piperazin- 1 -yl)-2-phenylethane- 1 ,2-dione 4-(4-fluoro-3-(piperazine-l -carbonyl)benzyl)phthalazin-l (2H)-one TFA salt(311mg, 0.65mmol),2-oxo-2-phenylacetic acid(900mg,6mmol), DIPEA(2ml, 11.6mmol),and HATU(1010mg, 2.65mmol) were mixed in DMF (50ml), the resulting reaction mixture was stirred at room temperature for 4 days until the reaction finished (monitored by TLC). The reaction mixture was then partitioned between DCM and water (100ml each, the water phase was extracted with DCM (100ml)). The combined organic phase was washed with water, sat. aqueous sodium bicarbonate, and brine, dried over sodium sulphate, filtered, and concentrated to yield the crude product. Then the crude product was firstly purified by column chromatography on silica gel (DCM:MeOH= 100: 1 ) and re-purified by preparative TLC (DCM:MeOH=40:l) to afford the desired product (1 lOmg, 32.9percent) as an off white solid.m/z [M+l ]+ 499.1HNMR(CDC13): δ 10.15 (1H, brs), 8.49-8.42 (1H, m), 7.95-7.91

(2H, m), 7.77-7.66 (4H, m), 7.64-7.48 (2H, m), 7.33-7.25 (2H, m), 7.08-6.85 (1 H, m), 4.28-4.24 (2H, d), 3.98-3.32 (8H, m)

110 mg

With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-ylmethylene]-N-methylmethanaminium hexafluorophosphate in N,N-dimethyl-formamide

T=20°C; 96 h; Hide Experimental Procedure

SHANGHAI DE NOVO PHARMATECH CO LTD.; Gao, Daxin

Patent: US2013/224107 A1, 2013 ; Location in patent: Paragraph 0170; 0171; 0172 ; Title/Abstract Full Text Show Details

4:1-(4-(2-fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoyl)piperazin-1-yl)-2-phenylethane-1,2-dione

Example 4 1-(4-(2-fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoyl)piperazin-1-yl)-2-phenylethane-1,2-dione 4-(4-fluoro-3-(piperazine-1-carbonyl)benzyl)phthalazin-1(2H)-one TFA salt (311 mg, 0.65 mmol), 2-oxo-2-phenylacetic acid (900 mg, 6 mmol), DIPEA (2 ml, 11.6 mmol), and HATU (1010 mg, 2.65 mmol) were mixed in DMF (50 ml), the resulting reaction mixture was stirred at room temperature for 4 days until the reaction finished (monitored by TLC). The reaction mixture was then partitioned between DCM and water (100 ml each, the water phase was extracted with DCM (100 ml)). The combined organic phase was washed with water, sat. aqueous sodium bicarbonate, and brine, dried over sodium sulphate, filtered, and concentrated to yield the crude product. Then the crude product was firstly purified by column chromatography on silica gel (DCM:MeOH=100:1) and re-purified by preparative TLC (DCM:MeOH=40:1) to afford the desired product (110 mg, 32.9percent) as an off white solid. m/z [M+1]+ 499.1 1HNMR (CDCl ): δ 10.15 (1H, brs), 8.49-8.42 (1H, m), 7.95-7.91 (2H, m), 7.77-7.66 (4H, m), 7.64-7.48 (2H, m), 7.33-7.25 (2H, m), 7.08-6.85 (1H, m), 4.28-4.24 (2H, d), 3.98-3.32 (8H, m). 3

178

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Rx-ID: 33314212

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With N-ethyl-N,N-diisopropylamine; HATU in N,N-dimethyl-formamide

T=20°C; 85 h; Hide Experimental Procedure

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SHANGHAI DE NOVO PHARMATECH CO LTD.; GAO, Daxin

Patent: WO2012/71684 A1, 2012 ; Location in patent: Page/Page column 28 ; Title/Abstract Full Text Show Details

Example 71 -(4-(2-fluoro-5 -((4-0X0-3 ,4-dihydrophthalazin- 1 -yl)methy l)benzoyl)- 1 ,4-diazepan- 1 -yl )-2-phenylethane- 1 ,2-dione4-(3-(l,4-diazepane-l-carbonyl)-4-fluorobenzyl)phthalazin-l(2H)-one TFA salt (320mg, 0.65mmol), 2-oxo-2-phenylacetic acid(1.4g,9.32mmol),DIPEA(3ml, 17.4mmol),and HATU(1.8g, 4.72mmol) were mixed in DMF (50ml). After the resulting reaction mixture was stirred at room temperature for 85h, the reaction mixture was partition between DCM and water (100ml each). The aqueous phase was extracted with DCM (100ml), and the combined organic phase was washed with water, sat. aqueous sodium bicarbonate, and brine, dried over sodium sulphate, filtered, and concentrated to yield the crude product. Then the crude product was purified by preparative TLC (Petroleum ether : Ethyl Acetate=T :l to 1 :2) to afford the desired product (140 mg, 41percent) as a light yellow solid.m/z [M+l ]+ 513.4'HNMR(CDC13): δ 10.41 (1 H, brs), 8.46-8.38 (2H, m), 7.95-7.87 (2H, m), 7.79-7.60 (4H, m), 7.53-7.45 (2H, m), 7.39-7.22 (2H, m), 7.08-

6.95 (1H, m), 4.31-4.28 (2H, d), 3.93-3.30 (8H, m), 1.78-1.62 (2H, m)

140 mg

With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-ylmethylene]-N-methylmethanaminium hexafluorophosphate in N,N-dimethyl-formamide

T=20°C; 85 h; Hide Experimental Procedure

SHANGHAI DE NOVO PHARMATECH CO LTD.; Gao, Daxin

Patent: US2013/224107 A1, 2013 ; Location in patent: Paragraph 0179; 0180; 0181 ; Title/Abstract Full Text Show Details

7:1-(4-(2-fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoyl)-1,4-diazepan-1-yl)-2-phenylethane-1,2-dione

Example 7 1-(4-(2-fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoyl)-1,4-diazepan-1-yl)-2-phenylethane-1,2-dione 4-(3-(1,4-diazepane-1-carbonyl)-4-fluorobenzyl)phthalazin-1(2H)-one TFA salt (320 mg, 0.65 mmol), 2-oxo-2-phenylacetic acid (1.4 g, 9.32 mmol), DIPEA (3 ml, 17.4 mmol), and HATU (1.8 g, 4.72 mmol) were mixed in DMF (50 ml). After the resulting reaction mixture was stirred at room temperature for 85 h, the reaction mixture was partition between DCM and water (100 ml each). The aqueous phase was extracted with DCM (100 ml), and the combined organic phase was washed with water, sat. aqueous sodium bicarbonate, and brine, dried over sodium sulphate, filtered, and concentrated to yield the crude product. Then the crude product was purified by preparative TLC (Petroleum ether:Ethyl Acetate=1:1 to 1:2) to afford the desired product (140 mg, 41percent) as a light yellow solid. m/z [M+1]+ 513.4 1HNMR (CDCl ): δ 10.41 (1H, brs), 8.46-8.38 (2H, m), 7.95-7.87 (2H, m), 7.79-7.60 (4H, m), 7.53-7.45 (2H, m), 7.39-7.22 (2H, m), 7.08-6.95 (1H, m), 4.31-4.28 (2H, d), 3.93-3.30 (8H, m), 1.78-1.62 (2H, m). 3

179

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Rx-ID: 34021619

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86%

With Fe(III)(edta); dihydrogen peroxide; palladium diacetate; sodium hydroxide in water

T=20°C; pH=7.2 - 7.8; 0.166667 h;

Sharma, Sugandha; Khan, Imran A.; Saxena, Anil K.

Advanced Synthesis and Catalysis, 2013 , vol. 355, # 4 p. 673 - 678 Title/Abstract Full Text View citing articles Show Details

80%

With dipotassium peroxodisulfate; palladium diacetate; silver(l) oxide in dimethyl sulfoxide; N,N-dimethylformamide

T=20°C; 20 h; Inert atmosphere; Reagent/catalystSolventTemperature;

Wang, Hua; Guo, Li-Na; Duan, Xin-Hua

Organic Letters, 2012 , vol. 14, # 17 p. 4358 - 4361 Title/Abstract Full Text View citing articles Show Details

180

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Rx-ID: 34021657

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88%

With Fe(III)(edta); dihydrogen peroxide; palladium diacetate; sodium hydroxide in water

T=20°C; pH=7.2 - 7.8; 0.25 h;

Sharma, Sugandha; Khan, Imran A.; Saxena, Anil K.

Advanced Synthesis and Catalysis, 2013 , vol. 355, # 4 p. 673 - 678 Title/Abstract Full Text View citing articles Show Details

78%

With dipotassium peroxodisulfate; palladium diacetate; silver(l) oxide in dimethyl sulfoxide; N,N-dimethylformamide

T=20°C; Inert atmosphere;

Wang, Hua; Guo, Li-Na; Duan, Xin-Hua

Organic Letters, 2012 , vol. 14, # 17 p. 4358 - 4361 Title/Abstract Full Text View citing articles Show Details

181

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Rx-ID: 35820817

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70%

With palladium(II) trifluoroacetate; silver carbonate in DME

T=150°C; 24 h; Sealed tube; chemoselective reaction;

Miao, Jinmin; Ge, Haibo

Organic Letters, 2013 , vol. 15, # 12 p. 2930 - 2933 Title/Abstract Full Text View citing articles Show Details

With palladium(II) trifluoroacetate; silver carbonate in DME

T=150 - 165°C; regioselective reaction; Hide Experimental Procedure

Pan, Shulei; Zhou, Bo; Zhang, Yanghui; Shao, Changdong; Shi, Guangfa

Synlett, 2016 , vol. 27, # 2 art. no. ST-2015-W0600-L, p. 277 - 281 Title/Abstract Full Text View citing articles Show Details

(20) Synthesis of para-Benzoylated Arenes

182

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Rx-ID: 35820819

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80%

With palladium(II) trifluoroacetate; silver carbonate in DME

T=150°C; 24 h; Sealed tube; chemoselective reaction;

Miao, Jinmin; Ge, Haibo

Organic Letters, 2013 , vol. 15, # 12 p. 2930 - 2933 Title/Abstract Full Text View citing articles Show Details

With palladium(II) trifluoroacetate; silver carbonate in DME

T=150 - 165°C; regioselective reaction; Hide Experimental Procedure

Pan, Shulei; Zhou, Bo; Zhang, Yanghui; Shao, Changdong; Shi, Guangfa

Synlett, 2016 , vol. 27, # 2 art. no. ST-2015-W0600-L, p. 277 - 281 Title/Abstract Full Text View citing articles Show Details

(20) Synthesis of para-Benzoylated Arenes

183

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Rx-ID: 35820820

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63%

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With palladium(II) trifluoroacetate; silver carbonate in DME

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Miao, Jinmin; Ge, Haibo

T=130°C; 24 h; Sealed tube; chemoselective reaction;

Organic Letters, 2013 , vol. 15, # 12 p. 2930 - 2933 Title/Abstract Full Text View citing articles Show Details

With palladium(II) trifluoroacetate; silver carbonate in DME

T=150 - 165°C; regioselective reaction; Hide Experimental Procedure

Pan, Shulei; Zhou, Bo; Zhang, Yanghui; Shao, Changdong; Shi, Guangfa

Synlett, 2016 , vol. 27, # 2 art. no. ST-2015-W0600-L, p. 277 - 281 Title/Abstract Full Text View citing articles Show Details

(20) Synthesis of para-Benzoylated Arenes

184

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Rx-ID: 35820822

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71%

With palladium(II) trifluoroacetate; silver carbonate in DME

T=150°C; 24 h; Sealed tube; chemoselective reaction;

Miao, Jinmin; Ge, Haibo

Organic Letters, 2013 , vol. 15, # 12 p. 2930 - 2933 Title/Abstract Full Text View citing articles Show Details

With palladium(II) trifluoroacetate; silver carbonate in DME

T=150 - 165°C; regioselective reaction; Hide Experimental Procedure

Pan, Shulei; Zhou, Bo; Zhang, Yanghui; Shao, Changdong; Shi, Guangfa

Synlett, 2016 , vol. 27, # 2 art. no. ST-2015-W0600-L, p. 277 - 281 Title/Abstract Full Text View citing articles Show Details

(20) Synthesis of para-Benzoylated Arenes

185

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Rx-ID: 37094989

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84%

With water; oxygen in 1,4-dioxane

T=20°C; 48 h; Schlenk techniqueIrradiation;

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Xu, Wen-Tao; Huang, Bei; Dai, Jian-Jun; Xu, Jun; Xu, Hua-Jian

Organic Letters, 2016 , vol. 18, # 13 p. 3114 - 3117 Title/Abstract Full Text View citing articles Show Details

72%

With tris(1,10-phenanthroline)ruthenium(II) dichloride; oxygen in dimethyl sulfoxide

T=32°C; 36 h; IrradiationSchlenk technique;

Liu, Jie; Liu, Qiang; Yi, Hong; Qin, Chu; Bai, Ruopeng; Qi, Xiaotian; Lan, Yu; Lei, Aiwen

Angewandte Chemie - International Edition, 2014 , vol. 53, # 2 p. 502 - 506 Angew. Chem., 2014 , vol. 126, # 2 p. 512 - 516,5 Title/Abstract Full Text View citing articles Show Details

186

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Rx-ID: 37094992

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79%

With tris(1,10-phenanthroline)ruthenium(II) dichloride; oxygen in dimethyl sulfoxide

T=32°C; 36 h; IrradiationSchlenk technique;

Liu, Jie; Liu, Qiang; Yi, Hong; Qin, Chu; Bai, Ruopeng; Qi, Xiaotian; Lan, Yu; Lei, Aiwen

Angewandte Chemie - International Edition, 2014 , vol. 53, # 2 p. 502 - 506 Angew. Chem., 2014 , vol. 126, # 2 p. 512 - 516,5 Title/Abstract Full Text View citing articles Show Details

72%

With silver trifluoromethanesulfonate in water; acetonitrile

T=60°C; 24 h; Schlenk technique;

Xu, Xiao-Lan; Xu, Wen-Tao; Wu, Ji-Wei; He, Jian-Bo; Xu, Hua-Jian

Organic and Biomolecular Chemistry, 2016 , vol. 14, # 42 p. 9970 - 9973 Title/Abstract Full Text Show Details

55%

With water; oxygen in 1,4-dioxane

T=20°C; 48 h; Schlenk techniqueIrradiation;

Xu, Wen-Tao; Huang, Bei; Dai, Jian-Jun; Xu, Jun; Xu, Hua-Jian

Organic Letters, 2016 , vol. 18, # 13 p. 3114 - 3117 Title/Abstract Full Text View citing articles Show Details

187

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Rx-ID: 37094999

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66%

With tris(1,10-phenanthroline)ruthenium(II) dichloride; oxygen in dimethyl sulfoxide

T=32°C; 72 h; IrradiationSchlenk technique;

Liu, Jie; Liu, Qiang; Yi, Hong; Qin, Chu; Bai, Ruopeng; Qi, Xiaotian; Lan, Yu; Lei, Aiwen

Angewandte Chemie - International Edition, 2014 , vol. 53, # 2 p. 502 - 506 Angew. Chem., 2014 , vol. 126, # 2 p. 512 - 516,5 Title/Abstract Full Text View citing articles Show Details

64%

With water; oxygen in 1,4-dioxane

T=20°C; 48 h; Schlenk techniqueIrradiation;

Xu, Wen-Tao; Huang, Bei; Dai, Jian-Jun; Xu, Jun; Xu, Hua-Jian

Organic Letters, 2016 , vol. 18, # 13 p. 3114 - 3117 Title/Abstract Full Text View citing articles Show Details

60%

With silver trifluoromethanesulfonate in water; acetonitrile

T=60°C; 24 h; Schlenk technique;

Xu, Xiao-Lan; Xu, Wen-Tao; Wu, Ji-Wei; He, Jian-Bo; Xu, Hua-Jian

Organic and Biomolecular Chemistry, 2016 , vol. 14, # 42 p. 9970 - 9973 Title/Abstract Full Text Show Details

188

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Rx-ID: 37821191

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88%

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Wang, Fei; Yin, Handong; Cui, Jichun; Zhang, Yanwei; Geng, Honglin; Hong, Min

Journal of Organometallic Chemistry, 2014 , vol. 759, p. 83 - 91 Title/Abstract Full Text View citing articles Show Details

in ethanol

3 h; Reflux; Hide Experimental Procedure

4.3. Preparation of Schiff base ligand

Ethanol solution (20 mL) of benzoylformic acid (10 mmol,1.50 g) was added dropwise to an ethanol solution (40 mL) containing 3-hydroxy-2-naphthoic acid hydrazide (10 mmol, 2.02 g). The mixture was heated under reflux with stirring for 3 h. The crude product was precipitated when the solution cooled down. Then the product was filtered and washed with ethanol for three times. Yield: 88percent, M.p. 199-200°C. Anal. Calc. for C19H14N2O4 (334.33): C:68.26; H: 4.22; N: 8.38percent; found C: 68.35; H: 4.25; N: 8.34percent. IR (KBr,cm-1): 3413 (s, NH); 3252 (s, COOH); 1649 (s, C=O); 1596 (s, C=N).1H NMR (d-DMSO, ppm): 13.37 (s,1H, COOH),11.74 (s,1H, OH),11.45(s, 1H, NH), 8.68 (s, 1H, H1), 7.95 (d, 1H, J=4 Hz, H8), 7.77 (d, 2H,J=4 Hz, H12), 7.72 (d, 1H, J= 8Hz, H5), 7.52-7.44 (m, 3H, H13, H14),7.36-7.33 (m, 2H, H6, H7). 7.20 (s, 1H, H4), 13C NMR (d-DMSO, ppm):164.4 (COOH), 162.6 (C=N), 153.3 (C3), 144.3 (CONH), 136.8 (C10),135.0 (C11), 134.0, 130.2, 129.8, 129.2, 129.0, 128.5, 127.9, 126.3, 124.6(C7), 120.9 (C2), 111.3 (C4).

189

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Rx-ID: 37919757

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With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine in acetonitrile

T=20°C; Hide Experimental Procedure

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THOMAS HELLEDAYS STIFTELSE FÖR MEDICINSK FORSKNING; SCOBIE, Martin; HELLEDAY, Thomas; KOOLMEISTER, Tobias; JACQUES, Sylvain; DESROSES, Matthieu; JACQUES-CORDONNIER, Marie-Caroline

Patent: WO2014/84778 A1, 2014 ; Location in patent: Page/Page column 171 ; Title/Abstract Full Text Show Details

316:Example 316N-{3-[2-Amino-6-(methylami no) pyrimidin-4-yl]phenyl}-2-oxo-2-phenylacetam ide.

Example 316N-{3-[2-Amino-6-(methylami no) pyrimidin-4-yl]phenyl}-2-oxo-2-phenylacetam ide.To a solution of 6-(3-aminophenyl)-4-N-methyl-pyrimidine-2,4-diamine (0.42 mol)in acetonitrile (4 mL) was added successively 2-oxo-2-phenyl-acetic acid (0.9eq.), triethylamine (2.5 eq.) and n-propanephosphonic acid anhydride (T3P, 2.0eq.). The resulting mixture was stirred at rt overnight. The mixture wasconcentrated and purified by preparative HPLC. LCMS [M+H] 348; 1H NMR (400MHz, DMSO-d6) OH ppm 8.30 - 8.36 (1 H, m), 8.00 - 8.11 (2 H, m), 7.66 - 7.84 (3H, m), 7.59 - 7.66 (2 H, m), 7.45 (1 H, t, J=7.96 Hz), 6.90 (1 H, br. 5.), 6.19 (1 H,5), 6.01 (2 H, 5), 2.80 (3 H, d, J=4.80 Hz).

With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine in acetonitrile

T=20°C; Hide Experimental Procedure

THOMAS HELLEDAYS STIFTELSE FÖR MEDICINSK FORSKNING; SCOBIE, Martin; WALLNER, Olov; KOOLMEISTER, Tobias; VALLIN, Karl Sven Axel; HENRIKSSON, Carl Martin; HOMAN, Evert; HELLEDAY, Thomas; JACQUES, Sylvain; DESROSES, Matthieu; JACQUES-CORDONNIER, Marie-Caroline; FISKESUND, Roland Julius Yu

Patent: WO2015/187089 A1, 2015 ; Location in patent: Page/Page column 169 ; Title/Abstract Full Text Show Details

316:Example 316 N-{3-[2-Amino-6-(methylamino)pyrimidin-4-yl]phenyl}-2-oxo-2-phenylacetamide.

Example 316 N-{3-[2-Amino-6-(methylamino)pyrimidin-4-yl]phenyl}-2-oxo-2-phenylacetamide. To a solution of 6-(3-aminophenyl)-4-N-methyl-pyrimidine-2,4-diamine (0.42 mol) in acetonitrile (4 mL) was added successively 2-oxo-2-phenyl-acetic acid (0.9 equiv.), triethylamine (2.5 equiv.) and n-propanephosphonic acid anhydride (T3P, 2.0 equiv.). The resulting mixture was stirred at rt overnight. The mixture was concentrated and purified by preparative HPLC. LCMS [M+H]+ 348; 1 H NMR (400 MHz, DMSO-d ) δ ppm 8.30 - 8.36 (1 H, m), 8.00 -

8.1 1 (2 H, m), 7.66 - 7.84 (3 H, m), 7.59 - 7.66 (2 H, m), 7.45 (1 H, t, J=7.96 Hz), 6.90 (1 H, br. s.), 6.19 (1 H, s), 6.01 (2 H, s), 2.80 (3 H, d, J=4.80 Hz).

190

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Rx-ID: 38006282

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100%

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With Dowex Inert atmosphere; Hide Experimental Procedure

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Wagner, Valentin; Schulz, Peter S.; Wasserscheid, Peter

Journal of Molecular Liquids, 2014 , vol. 192, p. 177 - 184 Title/Abstract Full Text View citing articles Show Details

1:Experimental section

[(1R,2S)-N,N-dimethylephedrinium][phenylglyoxylate] (IL1) A 0.1 molar solution of [(1R,2S)-N,N-dimethylephedrinium][iodide] was eluted slowly over a Dowex 1 * 8-column, which was presaturated with [phenylglyoxylate]. The eluent was intermittently tested to be iodide free by Ag[NO3]. Afterwards, the column was rinsed with water and the combined solutions were dried using a rotary evaporator and HV. The product was obtained as a white solid in near quantitative yield.

191

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Rx-ID: 41975314

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90%

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With dipotassium peroxodisulfate; palladium(II) trifluoroacetate in diethylene glycol dimethyl ether

T=80°C; 20 h; Inert atmosphere; Catalytic behavior; regioselective reaction; Hide Experimental Procedure

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Zhang, Liang; Wang, Zhe; Guo, Peiyu; Sun, Wei; Li, Ya-Min; Sun, Meng; Hua, Chengwen

Tetrahedron Letters, 2016 , vol. 57, # 23 p. 2511 - 2514 Title/Abstract Full Text View citing articles Show Details

General catalytic procedure forortho-acylation of N-nitrosoaniline with α-keto acids.

75%

With ammonium peroxydisulfate; palladium diacetate in diethylene glycol dimethyl ether

T=20°C; 18 h; Sealed tube;

Wu, Yinuo; Sun, Lei; Chen, Yunyun; Zhou, Qian; Huang, Jia-Wu; Miao, Hui; Luo, Hai-Bin

Journal of Organic Chemistry, 2016 , vol. 81, # 3 p. 1244 - 1250 Title/Abstract Full Text View citing articles Show Details

192

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Rx-ID: 43006161

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76%

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Yan, Yan-Mei; Gao, Yun; Ding, Ming-Wu

Tetrahedron, 2016 , vol. 72, # 35 p. 5548 - 5557 Title/Abstract Full Text View citing articles Show Details

in methanol

T=20°C; Ugi Condensation; Hide Experimental Procedure

4.4. Synthesis of azides 10 via Ugi reaction

General procedure: Benzaldehyde 3 (R2Ph,0.212 g, 2 mmol), 2-oxopropanoic acid 9 (R3Me, 0.176 g, 2 mmol),and t-butylisocyanide 5 (R4t-Bu, 0.166 g, 2 mmol) were addedsequentially to a solution of 2-azidobenzenamine 2 (R1H, 0.268 g,2 mmol) in methanol (15 mL) at room temperature. The reactionmixture was stirred at ambient temperature for 24e48 h. After thesolvent was evaporated, the crude reaction mixture was purified bycolumn chromatography with EtOAc/petroleum (1:5) as the eluentto give azide 10a.

193

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Rx-ID: 43006162

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81%

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Yan, Yan-Mei; Gao, Yun; Ding, Ming-Wu

Tetrahedron, 2016 , vol. 72, # 35 p. 5548 - 5557 Title/Abstract Full Text View citing articles Show Details

in methanol

T=20°C; Ugi Condensation; Hide Experimental Procedure

4.4. Synthesis of azides 10 via Ugi reaction

194

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Rx-ID: 728436

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87%

With hydrazine in acetic acid

T=0°C; 0.25 h;

Ishimoto; Tsukinoki; Tsuge; Tashiro

Journal of Labelled Compounds and Radiopharmaceuticals, 1995 , vol. 36, # 3 p. 267 - 273 Title/Abstract Full Text View citing articles Show Details

With water; monohydrazine sulfate

Darapsky

Journal fuer Praktische Chemie (Leipzig), 1917 , vol. <2> 96, p. 258 Full Text Show Details

With sodium hydroxide; monohydrazine sulfate

Bouveault

Bulletin de la Societe Chimique de France, 1897 , vol. <3> 17, p. 363,371 Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1897 , vol. 124, p. 157 Full Text Show Details

195

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Rx-ID: 1557976

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100%

33%

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With NH4S2O8; sulfuric acid; silver nitrate in dichloromethane; water

T=40°C; 2.5 h;

Fontana, Francesca; Minisci, Francesco; Barbosa, Maria Claudia Nogueira; Vismara, Elena

Journal of Organic Chemistry, 1991 , vol. 56, # 8 p. 2866 - 2869 Title/Abstract Full Text View citing articles Show Details

DOV PHARMACEUTICAL, INC.

Patent: WO2005/84439 A1, 2005 ; Location in patent: Page/Page column 40 ; Title/Abstract Full Text Show Details

196

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Rx-ID: 24347897

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65%

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With sodium hydrogencarbonate; triethylamine in toluene

Hide Experimental Procedure

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Rohm and Haas Company

Patent: US6013836 A1, 2000 ; Title/Abstract Full Text Show Details

Preparation of N'-t-butyl-N-benzoyl-carbonyl-N'-benzoylhydrazine

Preparation of N'-t-butyl-N-benzoyl-carbonyl-N'-benzoylhydrazine N'-t-butyl-N-benzoylhydrazine (1 g), benzoyl formic acid (1 g), and methanesulfonyl chloride (0.7 g) were stirred in toluene (35 ml) and saturated sodium bicarbonate (15 ml) at approximately 5° C.

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Triethylamine was added slowly, dropwise to the reaction mixture, and slowly warmed to room temperature. After stirring for 1 hour, the reaction mixture was diluted with toluene (20 ml) and the organic layer was washed several times with water. The organic layers were dried over magnesium sulfate, filtered and the toluene rotavapped off to afford a white gum. The crude product was chromatographed on silica gel (G:230-400 mesh) using a methylene chloride ether solvent system as eluent to afford a 65percent yield of a white solid.

197

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Rx-ID: 29691245

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87%

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With dipotassium peroxodisulfate; bis(benzonitrile)palladium(II) dichloride; silver(l) oxide in 1,4dioxane; acetic acid; dimethyl sulfoxide

T=120°C; 16 h;

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Li, Mingzong; Ge, Haibo

Organic Letters, 2010 , vol. 12, # 15 p. 3464 - 3467 Title/Abstract Full Text View citing articles Show Details

198

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Rx-ID: 29691247

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95%

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With dipotassium peroxodisulfate; bis(benzonitrile)palladium(II) dichloride; silver(l) oxide in 1,4dioxane; acetic acid; dimethyl sulfoxide

T=120°C; 12 h;

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Li, Mingzong; Ge, Haibo

Organic Letters, 2010 , vol. 12, # 15 p. 3464 - 3467 Title/Abstract Full Text View citing articles Show Details