At room temperature, a mixture of 0.35 g (0.001 mol) of N-(2-bromo-4,6-difluorophenyl)-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide, 0.06 g (0.00005 mol) of tetrakis-(triphenylphosphine)-palladium, 0.32 g (0.0018 mol) of 4-[(methoxyimino)methyl]phenylboronic acid and 10 ml of 1,2-dimethoxyethane is admixed with a solution of 0.5 g (0.0047 mol) of sodium carbonate in 3 ml of water. The reaction mixture is then heated to reflux temperature and kept at this temperature for 15 h. For work-up, the reaction mixture is stirred into 200 ml of water. The resulting precipitate is filtered off with suction and dried. The residue that remains is chromatographed on silica gel using the mobile phase cyclohexane:ethyl acetate=1:1. Concentration of the eluate gives 0.20 g (48% of theory) of N-{3,5-difluoro-4′-[(methoxyimino)methyl]-1,1′-biphenyl-2-yl}-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide in the form of a solid of melting point 164 to 167° C.
