Dimethylformamide → HCID 86692435, compound

Participants

Reaction Conditions

Reaction Steps

Cyclopropylboronic acid (269 mg), tripotassium phosphate (1.61 g) and 1,1′-bis(diphenylphosphino)ferrocene-palladium (II) dichloride dichloromethane complex (124 mg) were added to a N,N-dimethylformamide solution (15 ml) of 1-(5-bromo-3-chloropyridin-2-yl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (1.03 g) described in Reference Example 44(2), and the mixture was stirred at 100° C. for six hours. The reaction solution was cooled to room temperature, diluted with water, filtered through Celite and the filtrate was extracted with ethyl acetate three times. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give 1-(3-chloro-5-cyclopropylpyridin-2-yl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (240 mg) as a pale yellow solid.

Provenance & Evidence