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

Base Information

• Chemical Name: ethyl 1-(2,6-difluorophenyl)-6-oxo-6,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxylate
• CAS No.: 1080562-53-3
• Molecular Formula: C₁₅H₁₁F₂N₃O₃
• Molecular Weight: 319.267

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

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

Chemical Property:

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

There total 5 articles about ethyl 1-(2,6-difluorophenyl)-6-oxo-6,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxylate 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: 100.0%

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

Guidance literature:

With piperidine; In ethanol; at 75 ℃; Inert atmosphere;

DOI:10.1021/jm100095x

Reference yield:

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

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: piperidine / ethanol

With piperidine; hydrogen; sodium hydroxide; In ethanol; water; acetic acid; 3: Knoevenagel condensation;

DOI:10.1021/op100205s

Reference yield:

5-amino-1-(2,6-difluorophenyl)-1H-pyrazole-4-carbonitrile (1188285-05-3) → ethyl 1-(2,6-difluorophenyl)-6-oxo-6,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxylate (1080562-53-3)

Guidance literature:

Multi-step reaction with 2 steps

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

2: piperidine / ethanol

With piperidine; hydrogen; In ethanol; water; acetic acid; 2: Knoevenagel condensation;

DOI:10.1021/op100205s

upstream raw materials:

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

diethyl malonate

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

C₁₂H₁₀F₂N₂O₆

Downstream raw materials:

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

5-(3-(cyclopropylamino)-6-methylbenzo[d]isoxazol-7-yl)-1-(2,6-difluorophenyl)-7-methyl-1H-pyrazolo[3.4-b]pyridin-6(7H)-one

C₁₃H₈BrF₂N₃S

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

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