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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 520690Generated: October 29, 2026

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

https://huagongshe.com/reaction/520690

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
Reactant4-Chloropyridine-2-carboxamideHCID 303543—
ReactantPotassium tert-butoxideHCID 23665647—
ReactantN-(2-chloro-5-fluoro-4-hydroxyphenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamideHCID 90033637—
SolventDimethylformamideHCID 6228—
Product4-(5-chloro-4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)-2-fluorophenoxy)picolinamideHCID 7305326560.5%

Reaction Conditions

Temperature120 °C

Reaction Steps

To a suspension of N-(2-chloro-5-fluoro-4-hydroxyphenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide (751.6 mg, 2 mmol) and t-BuOK (224.4 mg, 2 mmol) in DMF (4 mL) and was added 4-chloropicolinamide (313.2 mg, 2 mmol). The reaction was warmed up to 120° C. and stirred for 15 hours. After the mixture cooling to rt, H2O (40 mL) was added and the resulted mixture was stirred at rt overnight. Filtered and the filter cake was purified by a silica gel column chromatography (DCM/CH3OH (v/v)=50/1) to give the title compound as a light yellow solid (290 mg, 60.5%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09326975B2
Source datasetuspto-grants-2016_05
ORD IDord-d37b10b3a8d746f8b0910fa033704d88
Source noteuspto-grants-2016_05