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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2047498Generated: October 26, 2026

Potassium Carbonate → 4'-(2,6-Difluoro-benzoylamino)-6-methyl-biphenyl-3-carboxylic acid methyl ester

https://huagongshe.com/reaction/2047498

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPotassium CarbonateHCID 11430—
ReactantMethyl 3-bromo-4-methylbenzoateHCID 7015747—
Reactant2,6-difluoro-N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]benzamideHCID 53414211—
SolventN-methyl-2-pyrrolidoneHCID 13387—
Product4'-(2,6-Difluoro-benzoylamino)-6-methyl-biphenyl-3-carboxylic acid methyl esterHCID 1155265875%

Reaction Conditions

Temperature120 °C

Reaction Steps

A suspension of 2,6-difluoro-N-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-benzamide (359 mg, 1 mmol), 3-bromo-4-methyl-benzoic acid methyl ester (228 mg, 1 mmol), benzyl(chloro)bis(triphenylphosphine)palladium (38 mg, 0.05 mmol) and K2CO3 (690 mg, 5 mmol) in 1-methylpyrrolidinone (NMP) (5 ml) was degassed with vacuum and heated at 120° C. for 10 hr. After cooling down to room temperature, ethyl acetate (EtOAc) (200 ml) was added and the mixture was washed with water (60 ml×3). The EtOAc was evaporated and the residue was purified by column chromatography on silica gel (Hexanes:EtOAc) to give Compound 1 (286 mg, yield 75%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08592486B2
Source datasetuspto-grants-2013_11
ORD IDord-8afd4206935246eb92863eb593fc3d1b
Source noteuspto-grants-2013_11