1H-Pyrrolo[2,3-c]pyridine-5-carboxylic acid, 4-(bromomethyl)-1-(phenylsulfonyl)-, methyl ester

Base Information

• Chemical Name: 1H-Pyrrolo[2,3-c]pyridine-5-carboxylic acid, 4-(bromomethyl)-1-(phenylsulfonyl)-, methyl ester
• CAS No.: 234430-88-7
• Molecular Formula: C₁₆H₁₃BrN₂O₄S
• Molecular Weight: 409.26
• DSSTox Substance ID: DTXSID101118297
• Mol file: 234430-88-7.mol

Synonyms:SCHEMBL2952576;DTXSID101118297;1H-Pyrrolo[2,3-c]pyridine-5-carboxylic acid, 4-(bromomethyl)-1-(phenylsulfonyl)-, methyl ester;234430-88-7

Chemical Property of 1H-Pyrrolo[2,3-c]pyridine-5-carboxylic acid, 4-(bromomethyl)-1-(phenylsulfonyl)-, methyl ester

Chemical Property:

• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 407.97794
• Heavy Atom Count: 24
• Complexity: 559

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)C1=NC=C2C(=C1CBr)C=CN2S(=O)(=O)C3=CC=CC=C3

Technology Process of 1H-Pyrrolo[2,3-c]pyridine-5-carboxylic acid, 4-(bromomethyl)-1-(phenylsulfonyl)-, methyl ester

There total 4 articles about 1H-Pyrrolo[2,3-c]pyridine-5-carboxylic acid, 4-(bromomethyl)-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: 61.0%

methyl 1-benzesulfonyl-4-methylpyrrolo<2,3-c>-pyridine-5-carboxylate (234430-86-5) → methyl 1-benzesulfonyl-4-bromomethylpyrrolo<2,3-c>-pyridine-5-carboxylate (234430-88-7)

Guidance literature:

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 4h; Heating;

DOI:10.1016/S0968-0896(99)00053-X

Reference yield:

methyl 2-amino-3,3-diethoxybutyrate (156571-72-1) → methyl 1-benzesulfonyl-4-bromomethylpyrrolo<2,3-c>-pyridine-5-carboxylate (234430-88-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 66 percent / Et₃N, 4 Angstroem MS / CH₂Cl₂ / 36 h / Ambient temperature

2: 98 percent / NaBH₃CN / ethanol / 0.83 h / Ambient temperature

3: 68 percent / TiCl₄ / benzene / 2 h / Heating

4: 61 percent / NBS, AIBN / CCl₄ / 4 h / Heating

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); 4 Angstroem MS; titanium tetrachloride; sodium cyanoborohydride; triethylamine; In tetrachloromethane; ethanol; dichloromethane; benzene;

DOI:10.1016/S0968-0896(99)00053-X

Reference yield:

2-{[1-(1-Benzenesulfonyl-1H-pyrrol-2-yl)-meth-(E)-ylidene]-amino}-3,3-diethoxy-butyric acid methyl ester (234430-85-4) → methyl 1-benzesulfonyl-4-bromomethylpyrrolo<2,3-c>-pyridine-5-carboxylate (234430-88-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / NaBH₃CN / ethanol / 0.83 h / Ambient temperature

2: 68 percent / TiCl₄ / benzene / 2 h / Heating

3: 61 percent / NBS, AIBN / CCl₄ / 4 h / Heating

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); titanium tetrachloride; sodium cyanoborohydride; In tetrachloromethane; ethanol; benzene;

DOI:10.1016/S0968-0896(99)00053-X

upstream raw materials:

methyl 1-benzesulfonyl-4-methylpyrrolo<2,3-c>-pyridine-5-carboxylate

methyl 2-amino-3,3-diethoxybutyrate

2-{[1-(1-Benzenesulfonyl-1H-pyrrol-2-yl)-meth-(E)-ylidene]-amino}-3,3-diethoxy-butyric acid methyl ester

methyl 2-<1-(benzesulfonylpyrrol-2-yl)methyl>amino-3,3-diethoxybutyrate

Downstream raw materials:

methyl 1-{[4-(benzyloxy)amino]methyl}-1-phenylsulfonyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylate