Methanol → 1-Benzyl-4-bromo-5-(3,5-difluoro-phenyl)-2-(2,4-difluoro-phenyl)-imidazole

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Reaction Steps

Reflux a mixture of 1-benzyl-4,5-dibromo-2-(2,4-difluoro-phenyl)-imidazole (0.386 g, 0.90 mmol), 3,5-difluorophenyl boronic acid (0.15 g, 0.945 mmol), trans-dichlorobis(triphenylphosphine) palladium (II) (0.065 g, 0.09 mmol), 2 M sodium carbonate (0.90 mL), methanol (1.5 mL) and toluene (10 mL) for 18 hours, then cool to ambient temperature. Dilute with ethyl acetate and wash with saturated sodium bicarbonate, saturated sodium chloride, dry with magnesium sulfate, filter and remove solvents under reduced pressure. Purify the residue on silica gel eluting with hexane/ethyl acetate mixtures to provide 1-benzyl-4-bromo-5-(3,5-difluoro-phenyl)-2-(2,4-difluoro-phenyl)-1H-imidazole (0.19 g). MS(ES+): m/z=461.0 (M+H)+

Provenance & Evidence