Ethyl 2-methyl-1H-indole-3-carboxylate [C12H13NO2] by Asch

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Reactions (44)

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Substances (50)

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Citations (36)

References

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in acetonitrile

T=20 - 25°C; 1.5 h; Inert atmosphereIrradiation; Hide Experimental Procedure

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Rx-ID: 47077307 Find similar reactions

Chaabouni; Pinkerton; Abid; Galaup; Chassaing

Synlett, 2017 , vol. 28, # 19 p. 2614 - 2618 Title/Abstract Full Text View citing articles Show Details

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.

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Rx-ID: 2402516 Find similar reactions

92%

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With copper(l) iodide; 1H-tetrazol-1-ylacetic acid; caesium carbonate in dimethyl sulfoxide

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

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Liu, Xiao-Guang; Li, Zi-Hao; Xie, Jian-Wei; Liu, Ping; Zhang, Jie; Dai, Bin

Tetrahedron, 2016 , vol. 72, # 5 p. 653 - 657 Title/Abstract Full Text View citing articles Show Details

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. 87%

With copper(I) oxide; caesium carbonate in water; dimethyl sulfoxide

T=100°C; 9 h; Inert atmosphere; regiospecific reaction;

Ali, Md Ashif; Punniyamurthy, Tharmalingam

Synlett, 2011 , # 5 art. no. D26210ST, p. 623 - 626 Title/Abstract Full Text View citing articles Show Details

57.5%

With copper(I) oxide; caesium carbonate in water; dimethyl sulfoxide

T=100°C; 16 h; Inert atmosphere; Time; Hide Experimental Procedure

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.

Patent: WO2013/120104 A2, 2013 ; Location in patent: Paragraph 00334 ; Title/Abstract Full Text Show Details

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).

15%

With copper(I) oxide; caesium carbonate in water; dimethyl sulfoxide

T=100°C; 9 h; Inert atmosphere; Hide Experimental Procedure

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, 2015 , vol. 25, # 17 p. 3644 - 3649 Title/Abstract Full Text View citing articles Show Details

Synthesis of N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-2-methyl-1-(1-phenylethyl)-1H-indole-3-carboxamide (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 3-oxobutanoate (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(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, 1984 , # 7 p. 616 - 617 Title/Abstract Full Text Show Details

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Rx-ID: 41597003 Find similar reactions

Multi-step reaction with 3 steps 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 View Scheme

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, 2015 , vol. 51, # 97 p. 17229 - 17232 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 3 steps 1: acetic acid / 1,4-dioxane / 110 °C 2: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver hexafluoroantimonate; acetic acid / 1,2-dichloro-ethane / 6 h / 60 °C / Sealed tube 3: sodium ethanolate / dimethyl sulfoxide / 24 h / 100 °C / Sealed tube; Inert atmosphere View Scheme

Jiang, Hui; Gao, Shang; Xu, Jinyi; Wu, Xiaoming; Lin, Aijun; Yao, Hequan

Advanced Synthesis and Catalysis, 2016 , vol. 358, # 2 p. 188 - 194 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 41658075 Find similar reactions

77%

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With copper(l) iodide; 1H-tetrazol-1-ylacetic acid; caesium carbonate in dimethyl sulfoxide

T=100°C; 12 h; Sealed tube; Catalytic behavior; Reagent/catalyst; Hide Experimental Procedure

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Liu, Xiao-Guang; Li, Zi-Hao; Xie, Jian-Wei; Liu, Ping; Zhang, Jie; Dai, Bin

Tetrahedron, 2016 , vol. 72, # 5 p. 653 - 657 Title/Abstract Full Text View citing articles Show Details

4.2 Typical procedure for the synthesis of 2,3-disubstituted indoles 3a–3t

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85%

With sodium ethanolate in dimethyl sulfoxide

T=100°C; 24 h; Sealed tubeInert atmosphere;

Jiang, Hui; Gao, Shang; Xu, Jinyi; Wu, Xiaoming; Lin, Aijun; Yao, Hequan

Advanced Synthesis and Catalysis, 2016 , vol. 358, # 2 p. 188 - 194 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 2 steps 1: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver hexafluoroantimonate; acetic acid / 1,2-dichloro-ethane / 6 h / 60 °C / Sealed tube 2: sodium ethanolate / dimethyl sulfoxide / 24 h / 100 °C / Sealed tube; Inert atmosphere View Scheme

Rx-ID: 41889026 Find similar reactions

Jiang, Hui; Gao, Shang; Xu, Jinyi; Wu, Xiaoming; Lin, Aijun; Yao, Hequan

Advanced Synthesis and Catalysis, 2016 , vol. 358, # 2 p. 188 - 194 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 41923671 Find similar reactions

Rx-ID: 41889005 Find similar reactions

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95%

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Stage #1: N-phenylacetamidine 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 atmosphereSealed tube; Stage #2: ethyl 2-diazo-3-oxobutanoate in 1,2-dichloro-ethane

T=40°C; 16 h; Inert atmosphereSealed tube; Catalytic behavior; Reagent/catalystTemperature;

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Li, Yunyun; Qi, Zisong; Wang, He; Yang, Xifa; Li, Xingwei

Angewandte Chemie - International Edition, 2016 , vol. 55, # 39 p. 11877 - 11881 Angew. Chem., 2016 , vol. 128, # 39 p. 12056 - 12060,5 Title/Abstract Full Text View citing articles Show Details

89%

With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; cesium acetate; acetic acid in 1,2-dichloro-ethane

T=80°C; 12 h; Reagent/catalyst;

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Rx-ID: 41923672 Find similar reactions

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With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; cesium acetate; acetic acid in 1,2-dichloro-ethane

T=80°C; 12 h;

Qi, Zisong; Yu, Songjie; Li, Xingwei

Organic Letters, 2016 , vol. 18, # 4 p. 700 - 703 Title/Abstract Full Text View citing articles Show Details

74%

Stage #1: N-phenylacetamidine 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 atmosphereSealed tube; Stage #2: ethyl 2-diazo-3-oxo-3-phenylpropanoate in 1,2-dichloro-ethane

T=80°C; 16 h; Inert atmosphereSealed tube;

Li, Yunyun; Qi, Zisong; Wang, He; Yang, Xifa; Li, Xingwei

Angewandte Chemie - International Edition, 2016 , vol. 55, # 39 p. 11877 - 11881 Angew. Chem., 2016 , vol. 128, # 39 p. 12056 - 12060,5 Title/Abstract Full Text View citing articles Show Details

Rx-ID: 41923673 Find similar reactions

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83%

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Qi, Zisong; Yu, Songjie; Li, Xingwei

Organic Letters, 2016 , vol. 18, # 4 p. 700 - 703 Title/Abstract Full Text View citing articles Show Details

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85%

With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; cesium acetate; acetic acid in 1,2-dichloro-ethane

T=80°C; 12 h;

Qi, Zisong; Yu, Songjie; Li, Xingwei

Organic Letters, 2016 , vol. 18, # 4 p. 700 - 703 Title/Abstract Full Text View citing articles Show Details

63%

Stage #1: N-phenylacetamidine 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 atmosphereSealed tube; Stage #2: ethyl 2-diazo-3-oxopentanoate in 1,2-dichloro-ethane

T=40°C; 16 h; Inert atmosphereSealed tube;

Li, Yunyun; Qi, Zisong; Wang, He; Yang, Xifa; Li, Xingwei

Angewandte Chemie - International Edition, 2016 , vol. 55, # 39 p. 11877 - 11881 Angew. Chem., 2016 , vol. 128, # 39 p. 12056 - 12060,5 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 43960102 Find similar reactions

37%

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Stage #1: N-phenylacetamidine 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 atmosphereSealed tube; Stage #2: ethyl 2-(bis(methoxy)phosphoryl)-2-diazoacetate in 1,2-dichloroethane

T=40°C; 16 h; Inert atmosphereSealed tube;

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Li, Yunyun; Qi, Zisong; Wang, He; Yang, Xifa; Li, Xingwei

Angewandte Chemie - International Edition, 2016 , vol. 55, # 39 p. 11877 - 11881 Angew. Chem., 2016 , vol. 128, # 39 p. 12056 - 12060,5 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 43960103 Find similar reactions

32%

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Stage #1: N-phenylacetamidine 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 atmosphereSealed tube; Stage #2: α-Aminocarbonyl-α-diazoessigsaeure-ethylester in 1,2-dichloroethane

T=80°C; 16 h; Inert atmosphereSealed tube;

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Li, Yunyun; Qi, Zisong; Wang, He; Yang, Xifa; Li, Xingwei

Angewandte Chemie - International Edition, 2016 , vol. 55, # 39 p. 11877 - 11881 Angew. Chem., 2016 , vol. 128, # 39 p. 12056 - 12060,5 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 41596964 Find similar reactions

63%

Stage #1: With methyl trifluoromethanesulfonate in dichloromethane

T=0 - 20°C; 24 h; Stage #2: With sodium hydroxide in ethanol; water

T=60°C; 12 h;

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, 2015 , vol. 51, # 97 p. 17229 - 17232 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 2 steps 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 View Scheme

Rx-ID: 41597035 Find similar reactions

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, 2015 , vol. 51, # 97 p. 17229 - 17232 Title/Abstract Full Text View citing articles Show Details

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70%

With sulfuric acid

T=-10 - 15°C; 3 h; Hide Experimental Procedure

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Rx-ID: 262050 Find similar reactions

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

Patent: WO2012/80447 A1, 2012 ; Location in patent: Page/Page column 34 ; Title/Abstract Full Text Show Details

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)

70%

With sulfuric acid

T=-10 - 15°C; 3 h; Hide Experimental Procedure

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

Patent: US2013/267555 A1, 2013 ; Location in patent: Paragraph 0168; 0171-0173 ; Title/Abstract Full Text Show Details

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

T=20°C;

Nef

Justus Liebigs Annalen der Chemie, 1891 , vol. 266, p. 75

Full Text View citing articles Show Details

Walker

American Chemical Journal, 1892 , vol. 14, p. 578 American Chemical Journal, 1894 , vol. 16, p. 435 Full Text View citing articles Show Details

9.4 g

With sulfuric acid

T=-5 - 0°C; 0.583333 h;

Dhayalan, Vasudevan; Clement, J. Arul; Jagan, Radhakrishnan; Mohanakrishnan, Arasambattu K.

European Journal of Organic Chemistry, 2009 , # 4 p. 531 - 546 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 21973146 Find similar reactions

Multi-step reaction with 2 steps 1: 82 percent / TsOH / benzene / Heating 2: 73 percent / Et3N / Pd(OAc)2 / dimethylformamide / 8 h / 120 °C View Scheme

Sakamoto, Takao; Nagano, Tatsuo; Kondo, Yoshinori; Yamanaka, Hiroshi

Synthesis, 1990 , # 3 p. 215 - 218 Title/Abstract Full Text Show Details

Multi-step reaction with 2 steps 1: 70 percent / TsOH / benzene / Heating 2: 65 percent / Et3N, P(2-CH3C6H4)3 / Pd(OAc)2 / dimethylformamide / 120 °C View Scheme

Sakamoto, Takao; Nagano, Tatsuo; Kondo, Yoshinori; Yamanaka, Hiroshi

Synthesis, 1990 , # 3 p. 215 - 218 Title/Abstract Full Text Show Details

Multi-step reaction with 2 steps 1: diethyl ether 2: concentrated sulfuric acid / 20 °C View Scheme

Nef

Justus Liebigs Annalen der Chemie, 1891 , vol. 266, p. 75 Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: acetic acid / tert-butyl methyl ether / 1 h / 0 °C 2: sulfuric acid / 3 h / -10 - 15 °C View Scheme

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

Patent: WO2012/80447 A1, 2012 ;

Multi-step reaction with 2 steps 1: tert-butyl methyl ether; acetic acid / 1 h / 0 °C 2: sulfuric acid / 3 h / -10 - 15 °C View Scheme

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

Patent: US2013/267555 A1, 2013 ;

Title/Abstract Full Text Show Details

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Rx-ID: 30159380 Find similar reactions

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Multi-step reaction with 2 steps 1: potassium carbonate / water; N,N-dimethyl-formamide / 20 °C 2: copper diacetate; caesium carbonate / N,N-dimethyl-formamide / 1 h / 125 °C View Scheme

Gao, Detian; Parvez, Masood; Back, Thomas G.

Chemistry - A European Journal, 2010 , vol. 16, # 48 p. 14281 - 14284 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 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 View Scheme

Gao, Detian; Back, Thomas G.

Chemistry - A European Journal, 2012 , vol. 18, # 46 p. 14828 - 14840 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 32879997 Find similar reactions

70%

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Stage #1: With potassium carbonate in 1,4-dioxane

T=100°C; 8 h; Stage #2: With copper(l) iodide in 1,4-dioxane

T=20 - 120°C; 7 h;

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Wang, Xianxue; Liu, Jin; Guo, Han; Ma, Chao; Gao, Xiai; Zhou, Kang; Huang, Guosheng

Synthesis, 2012 , vol. 44, # 7 p. 1037 - 1042 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 34417641 Find similar reactions

81%

With copper diacetate; caesium carbonate in N,N-dimethyl-formamide

T=125°C; 3 h;

Gao, Detian; Back, Thomas G.

Chemistry - A European Journal, 2012 , vol. 18, # 46 p. 14828 - 14840 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 34541145 Find similar reactions

63%

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With potassium chloride; oxygen; copper diacetate in methanol

T=50°C; Chan-Lam Coupling;

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Bunescu, Ala; Wang, Qian; Zhu, Jieping

Synthesis (Germany), 2012 , vol. 44, # 24 art. no. SS-2012-Z0772-OP, p. 3811 - 3814 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 30754670 Find similar reactions

A: 62% B: 31%

With iron; acetic acid

1 h; Reflux;

Janreddy, Donala; Kavala, Veerababurao; Bosco, J. W. John; Kuo, Chun-Wei; Yao, Ching-Fa

European Journal of Organic Chemistry, 2011 , # 12 p. 2360 - 2365 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 30754679 Find similar reactions

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Multi-step reaction with 2 steps 1: potassium carbonate / dimethyl sulfoxide / 80 - 90 °C 2: iron; acetic acid / 1 h / Reflux View Scheme

Janreddy, Donala; Kavala, Veerababurao; Bosco, J. W. John; Kuo, Chun-Wei; Yao, Ching-Fa

European Journal of Organic Chemistry, 2011 , # 12 p. 2360 - 2365 Title/Abstract Full Text View citing articles Show Details

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71%

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With copper diacetate; palladium diacetate; potassium carbonate in N,Ndimethyl-formamide

T=140°C; 0.25 h; Inert atmosphere;

Rx-ID: 31262007 Find similar reactions

Neumann, Julia J.; Rakshit, Souvik; Droege, Thomas; Wuertz, Sebastian; Glorius, Frank

Chemistry - A European Journal, 2011 , vol. 17, # 26 p. 7298 - 7303 Title/Abstract Full Text View citing articles Show Details

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81%

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With copper diacetate; caesium carbonate in N,N-dimethyl-formamide

T=125°C; 1 h;

Rx-ID: 30159367 Find similar reactions

Gao, Detian; Parvez, Masood; Back, Thomas G.

Chemistry - A European Journal, 2010 , vol. 16, # 48 p. 14281 - 14284 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 28221555 Find similar reactions

A: 79% B: 17%

With tetrakis(triphenylphosphine) palladium(0); silver orthophosphate in dimethyl sulfoxide

Maruyama, Jun; Yamashita, Hiromichi; Watanabe, Takeshi; Arai, Shigeru; Nishida, Atsushi

Tetrahedron, 2009 , vol. 65, # 7 p. 1327 - 1335

Title/Abstract Full Text View citing articles Show Details

T=100°C; Heck reaction; 3.5 h;

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Rx-ID: 10793079 Find similar reactions

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With copper(l) iodide in N,N-dimethyl-formamide

T=120°C; Hide Experimental Procedure

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FibroGen, Inc.

Patent: US2008/4309 A1, 2008 ; Location in patent: Page/Page column 31 ; Title/Abstract Full Text Show Details

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).

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Rx-ID: 28191218 Find similar reactions

58%

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Stage #1: Acetanilid With 2-chloropyridine; 2,6dichloropyridine; trifluoromethylsulfonic anhydride in dichloromethane

T=-78 - 0°C; Inert atmosphere; Stage #2: diazoacetic acid ethyl ester in dichloromethane

T=-30°C; 0.333333 h; Inert atmosphere;

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Cui, Sun-Liang; Wang, Jing; Wang, Yan-Guang

Journal of the American Chemical Society, 2008 , vol. 130, # 41 p. 13526 - 13527 Title/Abstract Full Text View citing articles Show Details

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71%

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With copper diacetate; palladium diacetate; potassium carbonate in N,Ndimethyl-formamide

T=140°C; 0.25 h; Inert atmosphere;

Rx-ID: 28213647 Find similar reactions

Wuertz, Sebastian; Rakshit, Souvik; Neumann, Julia J.; Droege, Thomas; Glorius, Frank

Angewandte Chemie - International Edition, 2008 , vol. 47, # 38 p. 7230 - 7233 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 10504270 Find similar reactions

A: 4920 mg B: 640 mg C: 480 mg D: 3190 mg

With sulfuric acid

T=-5°C; 0.5 h;

Bevk, David; Svete, Jurij; Stanovnik, Branko

Journal of Heterocyclic Chemistry, 2005 , vol. 42, # 7 p. 1413 - 1415 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 9254623 Find similar reactions

345 mg

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Stage #1: ethyl acetoacetate With potassium tert-butylate in various solvent(s) 0.166667 h;

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Bunce, Richard A.; Randall, Marty H.; Applegate, Kirby G.

Organic Preparations and Procedures International, 2002 , vol. 34, # 5 p. 493 - 499 Title/Abstract Full Text Show Details

Stage #2: ortho-nitrofluorobenzene in various solvent(s) T=65 - 70°C; 0.5 h; Stage #3: With iron; acetic acid

T=115°C;

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65%

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With triethylamine; tris-(o-tolyl)phosphine; palladium diacetate in N,Ndimethyl-formamide

T=120°C;

Rx-ID: 2222897 Find similar reactions

Sakamoto, Takao; Nagano, Tatsuo; Kondo, Yoshinori; Yamanaka, Hiroshi

Synthesis, 1990 , # 3 p. 215 - 218 Title/Abstract Full Text Show Details

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73%

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With triethylamine; palladium diacetate in N,N-dimethyl-formamide

T=120°C; 8 h;

Rx-ID: 2222898 Find similar reactions

Sakamoto, Takao; Nagano, Tatsuo; Kondo, Yoshinori; Yamanaka, Hiroshi

Synthesis, 1990 , # 3 p. 215 - 218 Title/Abstract Full Text Show Details

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Multi-step reaction with 2 steps 1: 82 percent / TsOH / benzene / Heating 2: 73 percent / Et3N / Pd(OAc)2 / dimethylformamide / 8 h / 120 °C View Scheme

Rx-ID: 21942208 Find similar reactions

Sakamoto, Takao; Nagano, Tatsuo; Kondo, Yoshinori; Yamanaka, Hiroshi

Synthesis, 1990 , # 3 p. 215 - 218 Title/Abstract Full Text Show Details

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Multi-step reaction with 2 steps 1: 70 percent / TsOH / benzene / Heating 2: 65 percent / Et3N, P(2-CH3C6H4)3 / Pd(OAc)2 / dimethylformamide / 120 °C View Scheme

Rx-ID: 21976293 Find similar reactions

Sakamoto, Takao; Nagano, Tatsuo; Kondo, Yoshinori; Yamanaka, Hiroshi

Synthesis, 1990 , # 3 p. 215 - 218 Title/Abstract Full Text Show Details

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With triethyl phosphite

Rx-ID: 2195143 Find similar reactions

Wadia, M. S.; Mali, R. S.; Tilve, S. G.; Yadav, V. J.

Synthesis, 1987 , # 4 p. 401 - 404 Title/Abstract Full Text Show Details

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Rx-ID: 3264886 Find similar reactions

60%

With lithium tert-butoxide in tert-butyl alcohol

T=82°C;

Spackamp, W. Nico

Heterocycles, 1984 , vol. 21, # 1 p. 211 - 234 Title/Abstract Full Text Show Details

60%

With lithium tert-butoxide in tert-butyl alcohol

5 h; Heating;

Dijkink, Jan; Zonjee, Johannes N.; Jong, Bart S. de; Speckamp, W. Nico

Heterocycles, 1983 , vol. 20, # 7 p. 1255 - 1258 Title/Abstract Full Text Show Details

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With sulfuric acid

T=-5°C; 0.5 h;

Rx-ID: 2836978 Find similar reactions

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 Title/Abstract Full Text Show Details

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Synthesize Find similar Rx-ID: 2931508 Find similar reactions

B: 245 mg C: 207 mg

With ammonia; sodium in diethyl ether

2 h; 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 Title/Abstract Full Text Show Details

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Rx-ID: 5453686 Find similar reactions

Hydroxylamin Ib, Ethylacetoacetat II;

Saeki et al.

Heterocycles, 1974 , vol. 2, p. 447,448 Full Text View citing articles Show Details

(yield)4-15percent;

Saeki et al.

Heterocycles, 1974 , vol. 2, p. 447,448 Full Text View citing articles Show Details

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Rx-ID: 287120 Find similar reactions

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With ethanol

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Houben; Fischer

Chemische Berichte, 1931 , vol. 64, p. 2636,2639 Full Text View citing articles Show Details

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With diethyl ether

Rx-ID: 5453687 Find similar reactions

Oddo

Gazzetta Chimica Italiana, 1912 , vol. 42 I, p. 371 Full Text View citing articles Show Details

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With diethyl ether

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Rx-ID: 5453688 Find similar reactions

Oddo

Gazzetta Chimica Italiana, 1912 , vol. 42 I, p. 371 Full Text View citing articles Show Details

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With sulfuric acid

T=-12°C;

Rx-ID: 480487 Find similar reactions Walker

American Chemical Journal, 1894 , vol. 16, p. 442 Full Text View citing articles Show Details

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Multi-step reaction with 2 steps 1: absolute diethyl ether 2: concentrated sulfuric acid / -12 °C View Scheme

Rx-ID: 22314905 Find similar reactions

Walker

American Chemical Journal, 1894 , vol. 16, p. 442 Full Text View citing articles Show Details

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Rx-ID: 5453689 Find similar reactions

Walker

American Chemical Journal, 1892 , vol. 14, p. 578 American Chemical Journal, 1894 , vol. 16, p. 435 Full Text View citing articles Show Details