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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 497992Generated: October 29, 2026

Water → 4,5-Difluoro-2-[[3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-yl]amino]benzoic acid

https://huagongshe.com/reaction/497992

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantPotassium CarbonateHCID 11430—
Reactant3-Methyl-1-(pyridin-2-yl)-1H-pyrazol-5-amineHCID 735132—
Reactant2-Chloro-4,5-difluorobenzoic acidHCID 737171—
CatalystCupric acetateHCID 8895—
SolventAcetic AcidHCID 176—
SolventDimethylformamideHCID 6228—
Product4,5-Difluoro-2-[[3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-yl]amino]benzoic acidHCID 2232019581%

Reaction Steps

Under an argon atmosphere, a solution of 3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-ylamine (6.01 g, 34.5 mmol), 2-chloro-4,5-difluorobenzoic acid (6.64 g, 34.5 mmol), copper acetate (II) (0.718 g, 3.95 mmol) and potassium carbonate (4.77 g, 34.5 mmol) in N,N-dimethylformamide (30 mL) was heated under reflux for 2 hours. The solution was cooled to room temperature, and poured into water. The solution was made weakly acidic by the addition of acetic acid, and the resulting crude crystals were collected by filtration. The crystals were washed with water and air dried to give the title compound (9.21 g, 81% yield).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06949648B2
Source datasetuspto-grants-2005_09
ORD IDord-93562eff33dc4f0482610bb09e6b1e61
Source noteuspto-grants-2005_09