1H-Pyrrolo[2,3-b]pyridine-3-carboxylic acid, 2-[[(cyanoMethyl)[(4-Methylphenyl)sulfonyl]aMino]Methyl]-5-fluoro-1-(phenylsulfonyl)-, Methyl ester

Base Information

• Chemical Name: 1H-Pyrrolo[2,3-b]pyridine-3-carboxylic acid, 2-[[(cyanoMethyl)[(4-Methylphenyl)sulfonyl]aMino]Methyl]-5-fluoro-1-(phenylsulfonyl)-, Methyl ester
• CAS No.: 1312755-50-2
• Molecular Formula: C₂₅H₂₁FN₄O₆S₂
• Molecular Weight: 556.595
• Mol file: 1312755-50-2.mol

Synonyms:1-benzenesulfonyl-5-fluoro-2-{[cyanomethyl-(toluene-4-sulfonyl)amino]methyl}-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid methyl ester

Chemical Property of 1H-Pyrrolo[2,3-b]pyridine-3-carboxylic acid, 2-[[(cyanoMethyl)[(4-Methylphenyl)sulfonyl]aMino]Methyl]-5-fluoro-1-(phenylsulfonyl)-, Methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1H-Pyrrolo[2,3-b]pyridine-3-carboxylic acid, 2-[[(cyanoMethyl)[(4-Methylphenyl)sulfonyl]aMino]Methyl]-5-fluoro-1-(phenylsulfonyl)-, Methyl ester

There total 7 articles about 1H-Pyrrolo[2,3-b]pyridine-3-carboxylic acid, 2-[[(cyanoMethyl)[(4-Methylphenyl)sulfonyl]aMino]Methyl]-5-fluoro-1-(phenylsulfonyl)-, Methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

1-benzenesulfonyl-5-fluoro-2-bromomethyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid methyl ester (1312755-49-9) + N-(cyanomethyl)-(4-methylphenyl)sulfonamide (20228-87-9) → 1-benzenesulfonyl-5-fluoro-2-{[cyanomethyl-(toluene-4-sulfonyl)amino]methyl}-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid methyl ester (1312755-50-2)

Guidance literature:

1-benzenesulfonyl-5-fluoro-2-bromomethyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid methyl ester; N-(cyanomethyl)-(4-methylphenyl)sulfonamide; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃;

With hydrogenchloride; In water; N,N-dimethyl-formamide; mineral oil;

Reference yield:

5-fluoro-2-methyl-1H-pyrrolo[2,3-b]pyridine (145934-92-5) → 1-benzenesulfonyl-5-fluoro-2-{[cyanomethyl-(toluene-4-sulfonyl)amino]methyl}-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid methyl ester (1312755-50-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: aluminum (III) chloride / dichloromethane / 0.83 h

1.2: 18 h

2.1: sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride / dichloromethane / 0 - 20 °C

3.1: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; 1,1'-azobis(1-cyanocyclohexanenitrile) / 1,2-dichloro-ethane / 17.5 h / 20 °C / Reflux

4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C

With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; N-benzyl-N,N,N-triethylammonium chloride; sodium hydride; sodium hydroxide; 1,1'-azobis(1-cyanocyclohexanenitrile); aluminum (III) chloride; In dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; mineral oil;

Reference yield:

2-amino-5-fluoropyridine (21717-96-4) → 1-benzenesulfonyl-5-fluoro-2-{[cyanomethyl-(toluene-4-sulfonyl)amino]methyl}-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid methyl ester (1312755-50-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sulfuric acid; potassium iodate / 100 °C

1.2: 1.5 h

2.1: triethylamine / copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 1 h / 0 - 20 °C

3.1: potassium tert-butylate / tert-butyl alcohol / 1 h / 85 °C

4.1: aluminum (III) chloride / dichloromethane / 0.83 h

4.2: 18 h

5.1: sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride / dichloromethane / 0 - 20 °C

6.1: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; 1,1'-azobis(1-cyanocyclohexanenitrile) / 1,2-dichloro-ethane / 17.5 h / 20 °C / Reflux

7.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C

With potassium iodate; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; sulfuric acid; potassium tert-butylate; N-benzyl-N,N,N-triethylammonium chloride; sodium hydride; triethylamine; sodium hydroxide; 1,1'-azobis(1-cyanocyclohexanenitrile); aluminum (III) chloride; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; mineral oil; tert-butyl alcohol;

upstream raw materials:

5-fluoro-2-methyl-1H-pyrrolo[2,3-b]pyridine

2-amino-5-fluoropyridine

1-benzenesulfonyl-5-fluoro-2-bromomethyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid methyl ester

N-(cyanomethyl)-(4-methylphenyl)sulfonamide

Downstream raw materials:

9-benzenesulfonyl-3-fluoro-5-hydroxy-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

9-benzenesulfonyl-5-chloro-3-fluoro-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile