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Date
44 reactions in Reaxys
2018-03-27 15h:55m:24s (EST)
NH
1. Query O O
Search as: As drawn
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O
O
NH
N N N
O
O
Rx-ID: 47077307 View in Reaxys 1/44 Yield 62 %
Conditions & References Typical Procedure General procedure: In a quartz tube under argon were successively added ortho-azidocinnamoyl derivative 1akand the appropriate solvent, with [1] = 3.2 mM. The resulting mixture was then irradiatedusing either the LUMOS 43® (1.5 h stirring time) or a conventional Tungsten lamp (6 hstirring time), as light sources. After evaporation of the solvent, purification of the crude bycolumn chromatography, eluting with an appropriate CY / EtOAc mixture, furnished thedesired photocyclized products 2a-k or 3/4 in pure forms. in acetonitrile, Time= 1.5h, T= 20 - 25 °C , Inert atmosphere, Irradiation Chaabouni; Pinkerton; Abid; Galaup; Chassaing; Synlett; vol. 28; nb. 19; (2017); p. 2614 - 2618 View in Reaxys
H 2N
I
NH
O
O O O
O
Rx-ID: 2402516 View in Reaxys 2/44 Yield 92 %
Conditions & References 4.2 Typical procedure for the synthesis of 2,3-disubstituted indoles 3a–3t General procedure: To a 10mL sealed tube was added CuI (0.05mmol), L4 (0.1mmol), ortho-iodo/bromoaniline (0.5mmol), β-keto ester/β-diketone (3.0mmol), Cs2CO3 (1.0mmol), and DMSO (1mL). The reaction mixture was reacted at 80°C in a preheated oil bath for 12h (for ortho-iodoanilines) or 36h (for ortho-bromoanilines). The reaction mixture was cooled to room temperature and extracted with ethyl acetate (3×20mL). The combined organic phases were washed with water and brine, dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatograph on silica gel (ethyl acetate/petroleum ether as the eluent) to afford the target products 3a–3s. With copper(l) iodide, 1H-tetrazol-1-ylacetic acid, caesium carbonate in dimethyl sulfoxide, Time= 12h, T= 80 °C , Sealed tube, Catalytic behavior, Reagent/catalyst, Solvent, Temperature Liu, Xiao-Guang; Li, Zi-Hao; Xie, Jian-Wei; Liu, Ping; Zhang, Jie; Dai, Bin; Tetrahedron; vol. 72; nb. 5; (2016); p. 653 - 657 View in Reaxys
87 %
With copper(I) oxide, caesium carbonate in water, dimethyl sulfoxide, Time= 9h, T= 100 °C , Inert atmosphere, regiospecific reaction Ali, Md Ashif; Punniyamurthy, Tharmalingam; Synlett; nb. 5; (2011); p. 623 - 626; Art.No: D26210ST View in Reaxys
57.5 %
36.1 : Step 1: Ethyl 2-methyi-lH4ndoie-3-carboxylate. Step 1: Ethyl 2-methyi-lH4ndoie-3-carboxylate.To a mixed solution of dimcthyl sulfoxide (100 mL) and water (34 mL), 24odobenzenamine (50 g, 228 mmol), ethyl 3-oxobutanoatc (35.6 g, 274 mmol), coppcr(i) oxide (3.3 g, 22.8 mmol) and cesium carbonate (75 g, 228 mmoi) was added. The mixture was stirred at 100°C for 16 hours under nitrogen gas atmosphere. The reaction mixture was filtered through a pad of cehte. The filtrate was diluted with water and extracted with ethyl acetate, The organic phase was concentrated in vacuo, and then the residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate = 5:1) to afford the title compound as a light yellow solid (26.6 g, 57.5percent), LCMS 204 (M + H). With copper(I) oxide, caesium carbonate in water, dimethyl sulfoxide, Time= 16h, T= 100 °C , Inert atmosphere, Time
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Patent; CONSTELLATION PHARMACEUTICALS; ALBRECHT, Brian, K.; AUDIA, James, Edmund; COOK, Andrew, S.; DAKIN, Les, A.; DUPLESSIS, Martin; GEHLING, Victor, S.; HARMANGE, Jean-Christophe; NAVESCHUK, Christopher, G.; VASWANI, Rishi, G.; WO2013/120104; (2013); (A2) English View in Reaxys 15 %
Synthesis of N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-2-methyl-1-(1-phenylethyl)-1H-indole-3carboxamide (9, 10, 11) Ethyl 2-methyl-1H-indole-3-carboxylate. In a pyrex vial a mixture of 2-iodobenzenamine (3.0 g, 13.7 mmol), ethyl 3oxobutanoate (2.0 g, 15.1 mmol), copper (I) oxide (0.2 g,1.4 mmol) and cesium carbonate (4.5 g, 13.7 mmol) were dissolved in DMSO:water (20 mL, 10:1) and heated at 100 °C for 9 h under anitrogen atmosphere. The reaction mixture was filtered through a pad of Celite and the filtrate diluted with water. The aqueous layer was extracted with EtOAc (3X) and the combined organic layer was dried over Na2SO4, filtered, and concentrated. The crude residue was purified by silicagel chromatography (petroleum ether/EtOAc = 5:1) to afford ethyl 2-methyl-1H-indole-3-carboxylate as a light yellow solid (0.42 g,15percent yield). With copper(I) oxide, caesium carbonate in water, dimethyl sulfoxide, Time= 9h, T= 100 °C , Inert atmosphere Gehling, Victor S.; Vaswani, Rishi G.; Nasveschuk, Christopher G.; Duplessis, Martin; Iyer, Priyadarshini; Balasubramanian, Srividya; Zhao, Feng; Good, Andrew C.; Campbell, Robert; Lee, Christina; Dakin, Les A.; Cook, Andrew S.; Gagnon, Alexandre; Harmange, Jean-Christophe; Audia, James E.; Cummings, Richard T.; Normant, Emmanuel; Trojer, Patrick; Albrecht, Brian K.; Bioorganic and Medicinal Chemistry Letters; vol. 25; nb. 17; (2015); p. 3644 - 3649 View in Reaxys With copper(l) iodide, sodium hydride, 1.) DMF, 2.) 120 deg C - 130 deg C, 7 h, Yield given. Multistep reaction Suzuki, Hitomi; Thiruvikraman, S. V.; Osuka, Atsuhiro; Synthesis; nb. 7; (1984); p. 616 - 617 View in Reaxys
NH
H 2N O
O
Rx-ID: 41597003 View in Reaxys 3/44 Yield
Conditions & References Reaction Steps: 3 1.1: 7 h / 160 °C 2.1: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate / methanol / 24 h / 60 °C / Sealed tube 3.1: methyl trifluoromethanesulfonate / dichloromethane / 24 h / 0 - 20 °C 3.2: 12 h / 60 °C With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer, silver(I) acetate, methyl trifluoromethanesulfonate in methanol, dichloromethane Mishra, Neeraj Kumar; Choi, Miji; Jo, Hyeim; Oh, Yongguk; Sharma, Satyasheel; Han, Sang Hoon; Jeong, Taejoo; Han, Sangil; Lee, Seok-Yong; Kim, In Su; Chemical Communications; vol. 51; nb. 97; (2015); p. 17229 17232 View in Reaxys Reaction Steps: 3 1: acetic acid / 1,4-dioxane / 110 °C 2: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver hexafluoroantimonate; acetic acid / 1,2-dichloroethane / 6 h / 60 °C / Sealed tube 3: sodium ethanolate / dimethyl sulfoxide / 24 h / 100 °C / Sealed tube; Inert atmosphere With silver hexafluoroantimonate, dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer, sodium ethanolate, acetic acid in 1,4-dioxane, dimethyl sulfoxide, 1,2-dichloro-ethane Jiang, Hui; Gao, Shang; Xu, Jinyi; Wu, Xiaoming; Lin, Aijun; Yao, Hequan; Advanced Synthesis and Catalysis; vol. 358; nb. 2; (2016); p. 188 - 194 View in Reaxys
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O
O O
NH
H 2N
Br O
O
Rx-ID: 41658075 View in Reaxys 4/44 Yield
Conditions & References
77 %
4.2 Typical procedure for the synthesis of 2,3-disubstituted indoles 3a–3t General procedure: To a 10mL sealed tube was added CuI (0.05mmol), L4 (0.1mmol), ortho-iodo/bromoaniline (0.5mmol), β-keto ester/β-diketone (3.0mmol), Cs2CO3 (1.0mmol), and DMSO (1mL). The reaction mixture was reacted at 80°C in a preheated oil bath for 12h (for ortho-iodoanilines) or 36h (for ortho-bromoanilines). The reaction mixture was cooled to room temperature and extracted with ethyl acetate (3×20mL). The combined organic phases were washed with water and brine, dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatograph on silica gel (ethyl acetate/petroleum ether as the eluent) to afford the target products 3a–3s. With copper(l) iodide, 1H-tetrazol-1-ylacetic acid, caesium carbonate in dimethyl sulfoxide, Time= 12h, T= 100 °C , Sealed tube, Catalytic behavior, Reagent/catalyst Liu, Xiao-Guang; Li, Zi-Hao; Xie, Jian-Wei; Liu, Ping; Zhang, Jie; Dai, Bin; Tetrahedron; vol. 72; nb. 5; (2016); p. 653 - 657 View in Reaxys
N
N NH
N
O
O
O
O
Rx-ID: 41889005 View in Reaxys 5/44 Yield
Conditions & References
85 %
With sodium ethanolate in dimethyl sulfoxide, Time= 24h, T= 100 °C , Sealed tube, Inert atmosphere Jiang, Hui; Gao, Shang; Xu, Jinyi; Wu, Xiaoming; Lin, Aijun; Yao, Hequan; Advanced Synthesis and Catalysis; vol. 358; nb. 2; (2016); p. 188 - 194 View in Reaxys
NH HN N
N
O
O
Rx-ID: 41889026 View in Reaxys 6/44 Yield
Conditions & References Reaction Steps: 2 1: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver hexafluoroantimonate; acetic acid / 1,2-dichloroethane / 6 h / 60 °C / Sealed tube 2: sodium ethanolate / dimethyl sulfoxide / 24 h / 100 °C / Sealed tube; Inert atmosphere With silver hexafluoroantimonate, dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer, sodium ethanolate, acetic acid in dimethyl sulfoxide, 1,2-dichloro-ethane Jiang, Hui; Gao, Shang; Xu, Jinyi; Wu, Xiaoming; Lin, Aijun; Yao, Hequan; Advanced Synthesis and Catalysis; vol. 358; nb. 2; (2016); p. 188 - 194 View in Reaxys
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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N
H N
HN
N O
NH
O O
O
O
Rx-ID: 41923671 View in Reaxys 7/44 Yield
Conditions & References
95 %
Stage 1: With silver hexafluoroantimonate, [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2, cesium acetate, acetic acid in 1,2-dichloro-ethane, Inert atmosphere, Sealed tube Stage 2: in 1,2-dichloro-ethane, Time= 16h, T= 40 °C , Inert atmosphere, Sealed tube, Catalytic behavior, Reagent/ catalyst, Temperature Li, Yunyun; Qi, Zisong; Wang, He; Yang, Xifa; Li, Xingwei; Angewandte Chemie - International Edition; vol. 55; nb. 39; (2016); p. 11877 - 11881; Angew. Chem.; vol. 128; nb. 39; (2016); p. 12056 - 12060,5 View in Reaxys
89 %
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer, cesium acetate, acetic acid in 1,2-dichloro-ethane, Time= 12h, T= 80 °C , Reagent/catalyst Qi, Zisong; Yu, Songjie; Li, Xingwei; Organic Letters; vol. 18; nb. 4; (2016); p. 700 - 703 View in Reaxys
HN
O
H N
O
NH
O N
O
O
N
Rx-ID: 41923672 View in Reaxys 8/44 Yield
Conditions & References
83 %
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer, cesium acetate, acetic acid in 1,2-dichloro-ethane, Time= 12h, T= 80 °C Qi, Zisong; Yu, Songjie; Li, Xingwei; Organic Letters; vol. 18; nb. 4; (2016); p. 700 - 703 View in Reaxys
74 %
Stage 1: With silver hexafluoroantimonate, [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2, cesium acetate, acetic acid in 1,2-dichloro-ethane, Inert atmosphere, Sealed tube Stage 2: in 1,2-dichloro-ethane, Time= 16h, T= 80 °C , Inert atmosphere, Sealed tube Li, Yunyun; Qi, Zisong; Wang, He; Yang, Xifa; Li, Xingwei; Angewandte Chemie - International Edition; vol. 55; nb. 39; (2016); p. 11877 - 11881; Angew. Chem.; vol. 128; nb. 39; (2016); p. 12056 - 12060,5 View in Reaxys
O
O
HN
H N
NH
O N O
N
O
Rx-ID: 41923673 View in Reaxys 9/44 Yield 85 %
Conditions & References With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer, cesium acetate, acetic acid in 1,2-dichloro-ethane, Time= 12h, T= 80 °C Qi, Zisong; Yu, Songjie; Li, Xingwei; Organic Letters; vol. 18; nb. 4; (2016); p. 700 - 703 View in Reaxys
63 %
Stage 1: With silver hexafluoroantimonate, [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2, cesium acetate, acetic acid in 1,2-dichloro-ethane, Inert atmosphere, Sealed tube Stage 2: in 1,2-dichloro-ethane, Time= 16h, T= 40 °C , Inert atmosphere, Sealed tube
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Li, Yunyun; Qi, Zisong; Wang, He; Yang, Xifa; Li, Xingwei; Angewandte Chemie - International Edition; vol. 55; nb. 39; (2016); p. 11877 - 11881; Angew. Chem.; vol. 128; nb. 39; (2016); p. 12056 - 12060,5 View in Reaxys
HN
H N
O
O N
P
N
NH O O
O
O
O
Rx-ID: 43960102 View in Reaxys 10/44 Yield
Conditions & References
37 %
Stage 1: With silver hexafluoroantimonate, [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2, cesium acetate, acetic acid in 1,2-dichloro-ethane, Inert atmosphere, Sealed tube Stage 2: in 1,2-dichloro-ethane, Time= 16h, T= 40 °C , Inert atmosphere, Sealed tube Li, Yunyun; Qi, Zisong; Wang, He; Yang, Xifa; Li, Xingwei; Angewandte Chemie - International Edition; vol. 55; nb. 39; (2016); p. 11877 - 11881; Angew. Chem.; vol. 128; nb. 39; (2016); p. 12056 - 12060,5 View in Reaxys
N
HN
N O
H N
NH
O O
O
NH 2
O
Rx-ID: 43960103 View in Reaxys 11/44 Yield
Conditions & References
32 %
Stage 1: With silver hexafluoroantimonate, [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2, cesium acetate, acetic acid in 1,2-dichloro-ethane, Inert atmosphere, Sealed tube Stage 2: in 1,2-dichloro-ethane, Time= 16h, T= 80 °C , Inert atmosphere, Sealed tube Li, Yunyun; Qi, Zisong; Wang, He; Yang, Xifa; Li, Xingwei; Angewandte Chemie - International Edition; vol. 55; nb. 39; (2016); p. 11877 - 11881; Angew. Chem.; vol. 128; nb. 39; (2016); p. 12056 - 12060,5 View in Reaxys
N NH
N
O
O
O
O
Rx-ID: 41596964 View in Reaxys 12/44 Yield 63 %
Conditions & References Stage 1: With methyl trifluoromethanesulfonate in dichloromethane, Time= 24h, T= 0 - 20 °C Stage 2: With sodium hydroxide in ethanol, water, Time= 12h, T= 60 °C Mishra, Neeraj Kumar; Choi, Miji; Jo, Hyeim; Oh, Yongguk; Sharma, Satyasheel; Han, Sang Hoon; Jeong, Taejoo; Han, Sangil; Lee, Seok-Yong; Kim, In Su; Chemical Communications; vol. 51; nb. 97; (2015); p. 17229 17232 View in Reaxys
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NH HN N
O
O
Rx-ID: 41597035 View in Reaxys 13/44 Yield
Conditions & References Reaction Steps: 2 1.1: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate / methanol / 24 h / 60 °C / Sealed tube 2.1: methyl trifluoromethanesulfonate / dichloromethane / 24 h / 0 - 20 °C 2.2: 12 h / 60 °C With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer, silver(I) acetate, methyl trifluoromethanesulfonate in methanol, dichloromethane Mishra, Neeraj Kumar; Choi, Miji; Jo, Hyeim; Oh, Yongguk; Sharma, Satyasheel; Han, Sang Hoon; Jeong, Taejoo; Han, Sangil; Lee, Seok-Yong; Kim, In Su; Chemical Communications; vol. 51; nb. 97; (2015); p. 17229 17232 View in Reaxys
O O
N
NH
H N
O
O
Rx-ID: 262050 View in Reaxys 14/44 Yield 70 %
Conditions & References 10.2 :The intermediate 18-1 (160 g) was added to cone. H2SO4 (800 ml) portionwise at -10°C under vigorous stirring. The solution was stirred for 1 h at -10°C and for 2 h at 15°C. The solution was poured into ice-water and extracted with tert-butyl methyl ether. After the solvent was removed, the solid was washed with petroleum ether. The intermediate 18-2 was obtained (80 g, 70percent) With sulfuric acid, Time= 3h, T= -10 - 15 °C Patent; JANSSEN RandD IRELAND; COOYMANS, Ludwig Paul; DEMIN, Samuel Dominique; HU, Lili; JONCKERS, Tim Hugo Maria; RABOISSON, Pierre Jean-Marie Bernard; TAHRI, Abdellah; VENDEVILLE, Sandrine Marie Helene; WO2012/80447; (2012); (A1) English View in Reaxys
70 %
10.2 : Step 2: Synthesis of ethyl 2-methyl-1H-indole-3-carboxylate 18-2 The intermediate 18-1 (160 g) was added to conc. H2SO4 (800 ml) portionwise at −10° C. under vigorous stirring. The solution was stirred for 1 h at −10° C. and for 2 h at 15° C. The solution was poured into ice-water and extracted with tert-butyl methyl ether. After the solvent was removed, the solid was washed with petroleum ether. The intermediate 18-2 was obtained (80 g, 70percent) With sulfuric acid, Time= 3h, T= -10 - 15 °C Patent; Janssen RandD Ireland; Cooymans, Ludwig Paul; Demin, Samuël Dominique; Hu, Lili; Jonckers, Tim Hugo Maria; Raboisson, Pierre Jean-Marie Bernard; Tahri, Abdellah; Vendeville, Sandrine Marie Helene; US2013/267555; (2013); (A1) English View in Reaxys With sulfuric acid, T= 20 °C Nef; Justus Liebigs Annalen der Chemie; vol. 266; (1891); p. 75 View in Reaxys Walker; American Chemical Journal; vol. 14; (1892); p. 578; American Chemical Journal; vol. 16; (1894); p. 435 View in Reaxys
9.4 g
With sulfuric acid, Time= 0.583333h, T= -5 - 0 °C
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Dhayalan, Vasudevan; Clement, J. Arul; Jagan, Radhakrishnan; Mohanakrishnan, Arasambattu K.; European Journal of Organic Chemistry; nb. 4; (2009); p. 531 - 546 View in Reaxys
NH
O
O O
O
O
Rx-ID: 21973146 View in Reaxys 15/44 Yield
Conditions & References Reaction Steps: 2 1: 82 percent / TsOH / benzene / Heating 2: 73 percent / Et3N / Pd(OAc)2 / dimethylformamide / 8 h / 120 °C With toluene-4-sulfonic acid, triethylamine, palladium diacetate in N,N-dimethyl-formamide, benzene Sakamoto, Takao; Nagano, Tatsuo; Kondo, Yoshinori; Yamanaka, Hiroshi; Synthesis; nb. 3; (1990); p. 215 - 218 View in Reaxys Reaction Steps: 2 1: 70 percent / TsOH / benzene / Heating 2: 65 percent / Et3N, P(2-CH3C6H4)3 / Pd(OAc)2 / dimethylformamide / 120 °C With toluene-4-sulfonic acid, triethylamine, tris-(o-tolyl)phosphine, palladium diacetate in N,N-dimethyl-formamide, benzene Sakamoto, Takao; Nagano, Tatsuo; Kondo, Yoshinori; Yamanaka, Hiroshi; Synthesis; nb. 3; (1990); p. 215 - 218 View in Reaxys Reaction Steps: 2 1: diethyl ether 2: concentrated sulfuric acid / 20 °C With diethyl ether, sulfuric acid Nef; Justus Liebigs Annalen der Chemie; vol. 266; (1891); p. 75 View in Reaxys Reaction Steps: 2 1: acetic acid / tert-butyl methyl ether / 1 h / 0 °C 2: sulfuric acid / 3 h / -10 - 15 °C With sulfuric acid, acetic acid in tert-butyl methyl ether Patent; JANSSEN RandD IRELAND; COOYMANS, Ludwig Paul; DEMIN, Samuel Dominique; HU, Lili; JONCKERS, Tim Hugo Maria; RABOISSON, Pierre Jean-Marie Bernard; TAHRI, Abdellah; VENDEVILLE, Sandrine Marie Helene; WO2012/80447; (2012); (A1) English View in Reaxys Reaction Steps: 2 1: tert-butyl methyl ether; acetic acid / 1 h / 0 °C 2: sulfuric acid / 3 h / -10 - 15 °C With sulfuric acid in tert-butyl methyl ether, acetic acid Patent; Janssen RandD Ireland; Cooymans, Ludwig Paul; Demin, Samuël Dominique; Hu, Lili; Jonckers, Tim Hugo Maria; Raboisson, Pierre Jean-Marie Bernard; Tahri, Abdellah; Vendeville, Sandrine Marie Helene; US2013/267555; (2013); (A1) English View in Reaxys
O
O
H N
I
O
NH
O
O
Rx-ID: 30159380 View in Reaxys 16/44
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Yield
Conditions & References Reaction Steps: 2 1: potassium carbonate / water; N,N-dimethyl-formamide / 20 °C 2: copper diacetate; caesium carbonate / N,N-dimethyl-formamide / 1 h / 125 °C With copper diacetate, potassium carbonate, caesium carbonate in water, N,N-dimethyl-formamide Gao, Detian; Parvez, Masood; Back, Thomas G.; Chemistry - A European Journal; vol. 16; nb. 48; (2010); p. 14281 - 14284 View in Reaxys Reaction Steps: 2 1: potassium carbonate / N,N-dimethyl-formamide; water / 48 h / 20 °C 2: caesium carbonate; copper diacetate / N,N-dimethyl-formamide / 3 h / 125 °C With copper diacetate, potassium carbonate, caesium carbonate in water, N,N-dimethyl-formamide Gao, Detian; Back, Thomas G.; Chemistry - A European Journal; vol. 18; nb. 46; (2012); p. 14828 - 14840 View in Reaxys
NH
H 2N
O O
I O
O
Rx-ID: 32879997 View in Reaxys 17/44 Yield
Conditions & References
70 %
Stage 1: With potassium carbonate in 1,4-dioxane, Time= 8h, T= 100 °C Stage 2: With copper(l) iodide in 1,4-dioxane, Time= 7h, T= 20 - 120 °C Wang, Xianxue; Liu, Jin; Guo, Han; Ma, Chao; Gao, Xiai; Zhou, Kang; Huang, Guosheng; Synthesis; vol. 44; nb. 7; (2012); p. 1037 - 1042 View in Reaxys
NH
Z
N H
I
O
O
O
O
Rx-ID: 34417641 View in Reaxys 18/44 Yield
Conditions & References
81 %
With copper diacetate, caesium carbonate in N,N-dimethyl-formamide, Time= 3h, T= 125 °C Gao, Detian; Back, Thomas G.; Chemistry - A European Journal; vol. 18; nb. 46; (2012); p. 14828 - 14840 View in Reaxys
H 2N O
O O
O
NH
B O
O
O
Rx-ID: 34541145 View in Reaxys 19/44 Yield 63 %
Conditions & References With potassium chloride, oxygen, copper diacetate in methanol, T= 50 °C , Chan-Lam Coupling Bunescu, Ala; Wang, Qian; Zhu, Jieping; Synthesis (Germany); vol. 44; nb. 24; (2012); p. 3811 - 3814; Art.No: SS-2012-Z0772-OP View in Reaxys
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O
N
O
NH
O
OH O
O
O
O
N OH
O
Rx-ID: 30754670 View in Reaxys 20/44 Yield
Conditions & References
62 %, 31 %
With iron, acetic acid, Time= 1h, Reflux Janreddy, Donala; Kavala, Veerababurao; Bosco, J. W. John; Kuo, Chun-Wei; Yao, Ching-Fa; European Journal of Organic Chemistry; nb. 12; (2011); p. 2360 - 2365 View in Reaxys
O
NH
I O
O
O
O
N O
O
O
O
N OH
Rx-ID: 30754679 View in Reaxys 21/44 Yield
Conditions & References Reaction Steps: 2 1: potassium carbonate / dimethyl sulfoxide / 80 - 90 °C 2: iron; acetic acid / 1 h / Reflux With iron, potassium carbonate, acetic acid in dimethyl sulfoxide Janreddy, Donala; Kavala, Veerababurao; Bosco, J. W. John; Kuo, Chun-Wei; Yao, Ching-Fa; European Journal of Organic Chemistry; nb. 12; (2011); p. 2360 - 2365 View in Reaxys
O
NH
O Z
H N O
O
Rx-ID: 31262007 View in Reaxys 22/44 Yield
Conditions & References
71 %
With copper diacetate, palladium diacetate, potassium carbonate in N,N-dimethyl-formamide, Time= 0.25h, T= 140 °C , Inert atmosphere Neumann, Julia J.; Rakshit, Souvik; Droege, Thomas; Wuertz, Sebastian; Glorius, Frank; Chemistry - A European Journal; vol. 17; nb. 26; (2011); p. 7298 - 7303 View in Reaxys
NH
Z
N I
O
O
O
O
O
Rx-ID: 30159367 View in Reaxys 23/44 Yield 81 %
Conditions & References With copper diacetate, caesium carbonate in N,N-dimethyl-formamide, Time= 1h, T= 125 °C Gao, Detian; Parvez, Masood; Back, Thomas G.; Chemistry - A European Journal; vol. 16; nb. 48; (2010); p. 14281 - 14284 View in Reaxys
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NH
I
NH
Z
N H O
O
O
O
O
O
Rx-ID: 28221555 View in Reaxys 24/44 Yield
Conditions & References
79 %, 17 %
With tetrakis(triphenylphosphine) palladium(0), silver orthophosphate in dimethyl sulfoxide, Time= 3.5h, T= 100 °C , Heck reaction Maruyama, Jun; Yamashita, Hiromichi; Watanabe, Takeshi; Arai, Shigeru; Nishida, Atsushi; Tetrahedron; vol. 65; nb. 7; (2009); p. 1327 - 1335 View in Reaxys
NH
H 2N
O–
O
Na + O
I
O
O
Rx-ID: 10793079 View in Reaxys 25/44 Yield
Conditions & References 26.a :a) 2-Methyl-1H-indole-3-carboxylic acid ethyl ester A mixture of 2-iodo-phenylamine (44.30 g, 202 mmol), sodium salt of ethyl acetoacetate (42.1 g, 263 mmol), and Cu(I)I (50.1 g, 263 mmol) in DMF (200 mL) was stirred at 120° C. overnight. Then the reaction mixture was cooled to room temperature, then diluted with methyl tert-butyl ether (MTBE) and water, and concentrated ammonia was added to dissolve the solid, the two layers were separated, the water layer was back extracted with MTBE; all MTBEs were combined and washed with sat. NaCl aqueous solution, dried over anhydrous sodium sulfate, filtered, and concentrated sequentially. The residue was crystallized in hexanes/EtOAc, giving the desired product (10.84 g), the mother liquor was concentrated and purified on column to give an additional batch of product (4.76 g). The title compound, 1H NMR (200 MHz, CDCl3): δ (ppm)=8.32 (1H), 8.09 (m, 1H), 7.31-7.13 (m, 3H), 4.39 (q, 2H, J=6.8 Hz), 2.74 (s, 3H), 1.45 (t, 3H, J=6.8 Hz). With copper(l) iodide in N,N-dimethyl-formamide, T= 120 °C Patent; FibroGen, Inc.; US2008/4309; (2008); (A1) English View in Reaxys
N
O
N
O
H N
NH
O O
O
Rx-ID: 28191218 View in Reaxys 26/44 Yield 58 %
Conditions & References Stage 1: With 2-chloropyridine, 2,6-dichloropyridine, trifluoromethylsulfonic anhydride in dichloromethane, T= -78 0 °C , Inert atmosphere Stage 2: in dichloromethane, Time= 0.333333h, T= -30 °C , Inert atmosphere Cui, Sun-Liang; Wang, Jing; Wang, Yan-Guang; Journal of the American Chemical Society; vol. 130; nb. 41; (2008); p. 13526 - 13527 View in Reaxys
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H N
O
NH
O O
O
Rx-ID: 28213647 View in Reaxys 27/44 Yield
Conditions & References
71 %
With copper diacetate, palladium diacetate, potassium carbonate in N,N-dimethyl-formamide, Time= 0.25h, T= 140 °C , Inert atmosphere Wuertz, Sebastian; Rakshit, Souvik; Neumann, Julia J.; Droege, Thomas; Glorius, Frank; Angewandte Chemie - International Edition; vol. 47; nb. 38; (2008); p. 7230 - 7233 View in Reaxys
O O
N
H N
NH
NH
NH
O
N
OH
O
O
N O
Rx-ID: 10504270 View in Reaxys 28/44 Yield
Conditions & References
4920 mg, 640 mg, 480 mg, 3190 mg
With sulfuric acid, Time= 0.5h, T= -5 °C Bevk, David; Svete, Jurij; Stanovnik, Branko; Journal of Heterocyclic Chemistry; vol. 42; nb. 7; (2005); p. 1413 1415 View in Reaxys
NH
F O
O
O N
O
O
O
O
Rx-ID: 9254623 View in Reaxys 29/44 Yield
Conditions & References
345 mg
Stage 1: With potassium tert-butylate in various solvent(s), Time= 0.166667h Stage 2: in various solvent(s), Time= 0.5h, T= 65 - 70 °C Stage 3: With iron, acetic acid, T= 115 °C Bunce, Richard A.; Randall, Marty H.; Applegate, Kirby G.; Organic Preparations and Procedures International; vol. 34; nb. 5; (2002); p. 493 - 499 View in Reaxys
O
E
H N
Br
NH
O O
O
Rx-ID: 2222897 View in Reaxys 30/44 Yield 65 %
Conditions & References With triethylamine, tris-(o-tolyl)phosphine, palladium diacetate in N,N-dimethyl-formamide, T= 120 °C Sakamoto, Takao; Nagano, Tatsuo; Kondo, Yoshinori; Yamanaka, Hiroshi; Synthesis; nb. 3; (1990); p. 215 - 218 View in Reaxys
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O
E
I
H N
NH
O
O
O
Rx-ID: 2222898 View in Reaxys 31/44 Yield
Conditions & References
73 %
With triethylamine, palladium diacetate in N,N-dimethyl-formamide, Time= 8h, T= 120 °C Sakamoto, Takao; Nagano, Tatsuo; Kondo, Yoshinori; Yamanaka, Hiroshi; Synthesis; nb. 3; (1990); p. 215 - 218 View in Reaxys
NH
H 2N
I
O
O
Rx-ID: 21942208 View in Reaxys 32/44 Yield
Conditions & References Reaction Steps: 2 1: 82 percent / TsOH / benzene / Heating 2: 73 percent / Et3N / Pd(OAc)2 / dimethylformamide / 8 h / 120 °C With toluene-4-sulfonic acid, triethylamine, palladium diacetate in N,N-dimethyl-formamide, benzene Sakamoto, Takao; Nagano, Tatsuo; Kondo, Yoshinori; Yamanaka, Hiroshi; Synthesis; nb. 3; (1990); p. 215 - 218 View in Reaxys
NH
H 2N
Br O
O
Rx-ID: 21976293 View in Reaxys 33/44 Yield
Conditions & References Reaction Steps: 2 1: 70 percent / TsOH / benzene / Heating 2: 65 percent / Et3N, P(2-CH3C6H4)3 / Pd(OAc)2 / dimethylformamide / 120 °C With toluene-4-sulfonic acid, triethylamine, tris-(o-tolyl)phosphine, palladium diacetate in N,N-dimethyl-formamide, benzene Sakamoto, Takao; Nagano, Tatsuo; Kondo, Yoshinori; Yamanaka, Hiroshi; Synthesis; nb. 3; (1990); p. 215 - 218 View in Reaxys
O
O O
N
O
NH
E
O
O
Rx-ID: 2195143 View in Reaxys 34/44 Yield
Conditions & References With triethyl phosphite Wadia, M. S.; Mali, R. S.; Tilve, S. G.; Yadav, V. J.; Synthesis; nb. 4; (1987); p. 401 - 404 View in Reaxys
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O
O
N
NH
Z
O
O O
O
O
Rx-ID: 3264886 View in Reaxys 35/44 Yield
Conditions & References
60 %
With lithium tert-butoxide in tert-butyl alcohol, T= 82 °C Spackamp, W. Nico; Heterocycles; vol. 21; nb. 1; (1984); p. 211 - 234 View in Reaxys
60 %
With lithium tert-butoxide in tert-butyl alcohol, Time= 5h, Heating Dijkink, Jan; Zonjee, Johannes N.; Jong, Bart S. de; Speckamp, W. Nico; Heterocycles; vol. 20; nb. 7; (1983); p. 1255 - 1258 View in Reaxys
O O
N H
NH
H N
O
O
Rx-ID: 2836978 View in Reaxys 36/44 Yield
Conditions & References
15.7 g
With sulfuric acid, Time= 0.5h, T= -5 °C Mills, Keith; Khawaja, Ibtisam K. Al; Al-Saleh, Fowzia; Joule, John A.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1981); p. 636 - 641 View in Reaxys
NH
NH
NH
N
O O
O
OH
O
Rx-ID: 2931508 View in Reaxys 37/44 Yield 245 mg, 207 mg
Conditions & References With ammonia, sodium in diethyl ether, Time= 2h, Heating Mills, Keith; Khawaja, Ibtisam K. Al; Al-Saleh, Fowzia; Joule, John A.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1981); p. 636 - 641 View in Reaxys
NH
O
O
Rx-ID: 5453686 View in Reaxys 38/44 Yield
Conditions & References Hydroxylamin Ib, Ethylacetoacetat II Saeki et al.; Heterocycles; vol. 2; (1974); p. 447,448 View in Reaxys (yield)4-15percent
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Saeki et al.; Heterocycles; vol. 2; (1974); p. 447,448 View in Reaxys
NH
NH
O– Na +
Cl Cl
O
O
Cl
O
Rx-ID: 287120 View in Reaxys 39/44 Yield
Conditions & References With ethanol Houben; Fischer; Chemische Berichte; vol. 64; (1931); p. 2636,2639 View in Reaxys
NH Cl
O
<2-methyl-indolyl-(1)>-magnesium iodide
O
O
O
Rx-ID: 5453687 View in Reaxys 40/44 Yield
Conditions & References With diethyl ether Oddo; Gazzetta Chimica Italiana; vol. 42 I; (1912); p. 371 View in Reaxys
NH Cl
O
<2-methyl-indolyl-(3)>-magnesium iodide
O
O
O
Rx-ID: 5453688 View in Reaxys 41/44 Yield
Conditions & References With diethyl ether Oddo; Gazzetta Chimica Italiana; vol. 42 I; (1912); p. 371 View in Reaxys
O E
O
N
NH
H N
O
O
Rx-ID: 480487 View in Reaxys 42/44 Yield
Conditions & References With sulfuric acid, T= -12 °C Walker; American Chemical Journal; vol. 16; (1894); p. 442 View in Reaxys
NH
O
O O
O
O
Rx-ID: 22314905 View in Reaxys 43/44
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Yield
Conditions & References Reaction Steps: 2 1: absolute diethyl ether 2: concentrated sulfuric acid / -12 °C With diethyl ether, sulfuric acid Walker; American Chemical Journal; vol. 16; (1894); p. 442 View in Reaxys
NH
I
silver salt of/the/ 2-methyl-indole-carboxylic acid-(3) O
O
Rx-ID: 5453689 View in Reaxys 44/44 Yield
Conditions & References Walker; American Chemical Journal; vol. 14; (1892); p. 578; American Chemical Journal; vol. 16; (1894); p. 435 View in Reaxys
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