N-(2,6-difluoro-3-hydroxy-phenyl)-3-fluoro-5-(3-fluorophenyl) benzamide → 2,4-Difluoro-3-[[3-fluoro-5-(3-fluorophenyl)phenyl]methylamino]phenol

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(2,6-difluoro-3-hydroxy-phenyl)-3-fluoro-5-(3-fluorophenyl)benzamide (390 mg, 1.1 mmol, 1.0 eq) in THF (6 mL) at 0° C. was added a solution of BH3 (1M in THF, 6.47 mL, 6.5 mmol, 6.0 eq). The reaction was heated to 60° C. and stirred overnight. The reaction mixture was quenched with water and extracted with EtOAc. The organic extract was washed with 5% NaHCO3, water and brine, dried (Na2SO4) and the solvent removed in vacuo to afford a crude residue which was purified by column chromatography (petroleum ether:EtOAc 1:0 to 10:1) to give the title compound as an oil (353 mg, 94%).

Provenance & Evidence