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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 520696Generated: October 27, 2026

Ethyl Acetate → 3-chloro-4-(4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)-3-fluorophenoxy)picolinamide

https://huagongshe.com/reaction/520696

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl AcetateHCID 8857—
Reactant3,4-Dichloropyridine-2-carboxamideHCID 23165143—
ReactantPotassium tert-butoxideHCID 23665647—
ReactantN-(2-fluoro-4-hydroxyphenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamideHCID 90032748—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
Product3-chloro-4-(4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)-3-fluorophenoxy)picolinamideHCID 7305107587%

Reaction Steps

A mixture of N-(2-fluoro-4-hydroxyphenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide (300 mg, 0.879 mmol) and t-BuOK (118 mg, 1.05 mmol) in DMF (3 mL) was stirred at rt for 30 minutes, then 3,4-dichloropicolinamide (201 mg, 1.05 mmol) was added. The reaction mixture was heated to 120° C. and stirred for 12 hours. EtOAc (1 mL) and H2O (20 mL) were added, and the resulted mixture was stirred at rt overnight. Filtered to give the title compound as a brown solid (379 mg, 87.0%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09326975B2
Source datasetuspto-grants-2016_05
ORD IDord-783fe0f1f9b547739bf178b84e9cafb8
Source noteuspto-grants-2016_05