Titanium chloride (2.86 ml; 26 mmol) was added portionwise to a solution of methyl 4-amino-2-(4-fluorophenyl)benzoate (5 g; 20 mmol), 1-(4-fluorophenyl)-2-(imidazol-1-yl) ethanone (4.08 g; 20 mmol) and triethylamine (8.4 ml; 60 mmol) in dichloromethane (120 ml) at 0° C. under argon atmosphere. After stirring overnight at ambient temperature, sodium cyanoborohydride (1.4 g; 0.22 mmol) in solution in methanol (10 ml) was added at 0° C. The reaction mixture was stirred for 2 hours at ambient temperature, treated with 5% aqueous sodium hydrogen carbonate solution, filtered and extracted with dichloromethane. After evaporation to dryness of the organic phase, the residue was purified by flash chromatography eluting with dichloromethane/ethanol 95/5 to give methyl 4-[1-(4-fluorophenyl)-2-(imidazol-1-yl)ethylamino]-2-(4-fluorophenyl)benzoate. Yield 52%.
