2-chloro-1-phenyl-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid

Base Information

• Chemical Name: 2-chloro-1-phenyl-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid
• CAS No.: 1175014-68-2
• Molecular Formula: C₁₄H₉ClN₂O₂
• Molecular Weight: 272.691
• Mol file: 1175014-68-2.mol

Synonyms:2-chloro-1-phenyl-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid

Chemical Property of 2-chloro-1-phenyl-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-chloro-1-phenyl-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid

There total 7 articles about 2-chloro-1-phenyl-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid 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: 88.0%

2-chloro-1-phenyl-1H-pyrrolo[3,2-b]pyridine-3-carbaldehyde (1175014-67-1) → 2-chloro-1-phenyl-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid (1175014-68-2)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; In tert-butyl alcohol; at 20 ℃;

DOI:10.1016/j.bmcl.2011.06.114

Reference yield:

1H-pyrrolo[3,2-b]pyridine (272-49-1) → 2-chloro-1-phenyl-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid (1175014-68-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 8-quinolinol; copper(l) iodide; potassium carbonate / dimethyl sulfoxide / 130 °C

2: bromine; tert-butyl alcohol / water / 20 °C

3: palladium on activated charcoal; hydrogen / ethanol / 20 °C

4: pyridine; trichlorophosphate / dichloromethane / 0 - 20 °C

5: trichlorophosphate / dichloromethane / 100 °C

6: sodium dihydrogenphosphate; sodium chlorite / tert-butyl alcohol / 20 °C

With pyridine; sodium chlorite; sodium dihydrogenphosphate; copper(l) iodide; 8-quinolinol; palladium on activated charcoal; hydrogen; bromine; potassium carbonate; tert-butyl alcohol; trichlorophosphate; In ethanol; dichloromethane; water; dimethyl sulfoxide; tert-butyl alcohol; 4: Vilsmeier-Haack reaction;

DOI:10.1016/j.bmcl.2011.06.114

Reference yield:

1-phenyl-1H-pyrrolo[3,2-b]pyridine (514182-79-7) → 2-chloro-1-phenyl-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid (1175014-68-2)

Guidance literature:

Multi-step reaction with 5 steps

1: bromine; tert-butyl alcohol / water / 20 °C

2: palladium on activated charcoal; hydrogen / ethanol / 20 °C

3: pyridine; trichlorophosphate / dichloromethane / 0 - 20 °C

4: trichlorophosphate / dichloromethane / 100 °C

5: sodium dihydrogenphosphate; sodium chlorite / tert-butyl alcohol / 20 °C

With pyridine; sodium chlorite; sodium dihydrogenphosphate; palladium on activated charcoal; hydrogen; bromine; tert-butyl alcohol; trichlorophosphate; In ethanol; dichloromethane; water; tert-butyl alcohol; 3: Vilsmeier-Haack reaction;

DOI:10.1016/j.bmcl.2011.06.114

upstream raw materials:

2-chloro-1-phenyl-1H-pyrrolo[3,2-b]pyridine-3-carbaldehyde

1H-pyrrolo[3,2-b]pyridine

1-phenyl-1H-pyrrolo[3,2-b]pyridine

1-phenyl-1,3-dihydro-pyrrolo[3,2-b]pyridin-2-one

Downstream raw materials:

4-(2-chloro-1-phenyl-1H-pyrrolo[3,2-b]pyridine-3-carbonyl)-piperazine-1-carboxylic acid tert-butyl ester

4-[2-(2-fluoro-6-methyl-phenoxy)-1-phenyl-1H-pyrrolo[3,2-b]pyridine-3-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester

4-[2-(3-fluoro-2-methyl-phenoxy)-1-phenyl-1H-pyrrolo[3,2-b]pyridine-3-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester

4-[2-(5-fluoro-2-methyl-phenoxy)-1-phenyl-1H-pyrrolo[3,2-b]pyridine-3-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester

Refernces

• 1、 -. "CYCLIC AZAINDOLE-3-CARBOXAMIDES, THEIR PREPARATION AND THEIR USE AS PHARMACEUTICALS". Page/Page column 65. . Retrieved 2009/09/05.