Methyl chlorodifluoroacetate → 3-n-Butyl-4-[(3-fluoro-2'-sulfamoylbiphenyl-4-yl)methyl]-1-[5-nitro-2-(trifluoromethyl)phenyl]-1H-pyrazole-5-carbonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-(2-bromo-5-nitrophenyl)-3-n-butyl-4-[(3-fluoro-2'-sulfamoylbiphenyl-4-yl)methyl]-1H-pyrazole-5-carbonitrile (from Step A) (1 equivalent), methyl chlorodifluoroacetate (2 equiv), potassium fluoride (1 equiv), cuprous iodide (1 equiv), potassium bromide (1 equiv), and DMF (approximately 3 mL per gram of pyrazole compound) is stirred under N2 in a sealed tube at 120° C. for about 15 hours. The cooled mixture is diluted with H2O and extracted a few times with ethyl acetate. The combined organic fractions are washed with brine, dried over Na2SO4, and filtered. The filtrate is concentrated, and the residue is chromatographed on silica gel (elution with CH2Cl2 --MeOH) to yield the title compound.

Provenance & Evidence