1-benzyl-4-chloro-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester

Base Information

• Chemical Name: 1-benzyl-4-chloro-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester
• CAS No.: 37801-55-1
• Molecular Formula: C₁₆H₁₄ClN₃O₂
• Molecular Weight: 315.759
• Mol file: 37801-55-1.mol

Synonyms:1-benzyl-4-chloro-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester

Chemical Property of 1-benzyl-4-chloro-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-benzyl-4-chloro-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester

There total 5 articles about 1-benzyl-4-chloro-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl 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: 65.0%

1-Benzyl-5-(2,2-bis-ethoxycarbonyl-vinyl-amino)pyrazol (37799-73-8) → 1-benzyl-4-chloro-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester (37801-55-1)

Guidance literature:

1-Benzyl-5-(2,2-bis-ethoxycarbonyl-vinyl-amino)pyrazol; With trichlorophosphate; at 130 ℃; for 8h;

With sodium hydroxide; In water; at 0 ℃; pH=7;

Reference yield:

1-benzyl-1H-pyrazol-5-amine (3528-51-6) + diethyl 2-ethoxymethylenemalonate (87-13-8) → 1-benzyl-4-chloro-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester (37801-55-1)

Guidance literature:

1-benzyl-1H-pyrazol-5-amine; diethyl 2-ethoxymethylenemalonate; at 160 ℃; for 5h;

With thionyl chloride;

DOI:10.1016/j.bmcl.2010.01.133

Reference yield:

1-benzyl-1H-pyrazol-5-amine (3528-51-6) → 1-benzyl-4-chloro-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester (37801-55-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 4 h / 120 °C

2.1: trichlorophosphate / 8 h / 130 °C

2.2: 0 °C / pH 7

With trichlorophosphate;

upstream raw materials:

1-benzyl-1H-pyrazol-5-amine

diethyl 2-ethoxymethylenemalonate

1-Benzyl-5-(2,2-bis-ethoxycarbonyl-vinyl-amino)pyrazol

Downstream raw materials:

C₂₆H₂₂ClN₅O₂

1-benzyl-4-(4-fluoro-2-methyl-phenyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester

N-[1-benzyl-4-(4-fluoro-2-methyl-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-isobutyramide

2-(3,5-bis-trifluoromethyl-phenyl)-N-[4-(4-fluoro-2-methyl-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-N-methyl-isobutyramide