1-(2,6-difluorophenyl)-6-oxo-6,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid

Base Information

• Chemical Name: 1-(2,6-difluorophenyl)-6-oxo-6,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid
• CAS No.: 1256346-80-1
• Molecular Formula: C₁₃H₇F₂N₃O₃
• Molecular Weight: 291.214

Synonyms:1-(2,6-difluorophenyl)-6-oxo-6,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid

Chemical Property of 1-(2,6-difluorophenyl)-6-oxo-6,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid

Chemical Property:

Purity/Quality:

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Technology Process of 1-(2,6-difluorophenyl)-6-oxo-6,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid

There total 5 articles about 1-(2,6-difluorophenyl)-6-oxo-6,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-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: 90.1%

5-amino-1-(2,6-difluorophenyl)-1H-pyrazole-4-carbaldehyde (1080562-66-8) + diethyl malonate (105-53-3) → 1-(2,6-difluorophenyl)-6-oxo-6,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid (1256346-80-1)

Guidance literature:

5-amino-1-(2,6-difluorophenyl)-1H-pyrazole-4-carbaldehyde; diethyl malonate; With piperidine; In ethanol; for 7h; Reflux; Large scale reaction;

With sulfuric acid; In acetic acid; Reflux;

DOI:10.1021/op100205s

Reference yield:

ethyl 1-(2,6-difluorophenyl)-6-oxo-6,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxylate (1080562-53-3) → 1-(2,6-difluorophenyl)-6-oxo-6,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid (1256346-80-1)

Guidance literature:

With lithium hydroxide monohydrate; water; In acetonitrile; at 20 - 90 ℃; Inert atmosphere;

DOI:10.1021/jm100095x

Reference yield:

1-(2,6-difluorophenyl)hydrazine hydrochloride → 1-(2,6-difluorophenyl)-6-oxo-6,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid (1256346-80-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydroxide / water; acetic acid / 4.2 h / 0 - 60 °C / Large scale reaction

2.1: hydrogen / water; acetic acid / 6.5 h / 1535.79 Torr / Autoclave; Large scale reaction

3.1: piperidine / ethanol / 7 h / Reflux; Large scale reaction

3.2: Reflux

With piperidine; hydrogen; sodium hydroxide; In ethanol; water; acetic acid; 3.1: Knoevenagel condensation;

DOI:10.1021/op100205s

upstream raw materials:

ethyl 1-(2,6-difluorophenyl)-6-oxo-6,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

5-amino-1-(2,6-difluorophenyl)-1H-pyrazole-4-carbaldehyde

diethyl malonate

C₁₂H₁₀F₂N₂O₆

Downstream raw materials:

5-bromo-1-(2,6-difluorophenyl)-1H-pyrazolo[3,4-b]pyridin-6(7H)-one

5-bromo-1-(2,6-difluorophenyl)-7-methyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one

C₁₃H₈BrF₂N₃O

3-(1-(2,6-difluorophenyl)-7-methyl-6-oxo-6,7-dihydro-1H-pyrazolo[3,4-b]pyridin-5-yl)-4-methylbenzoic acid

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