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

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(2,6-difluoro-3-hydroxy-phenyl)-5-(3-fluorophenyl)-2-methoxy-3-methyl-benzamide (150 mg, 0.39 mmol, 1.0 eq) in THF (3 mL) at 0° C. was added a solution of BH3 (1M in THF, 2.32 mL, 2.32 mmol, 5.9 eq). The reaction was heated at 60° C. overnight, then quenched by addition of water. The aqueous layer was extracted with EtOAc and the organic extract was washed with 5% Na2CO3, water and brine, dried (Na2SO4), filtered and evaporated in vacuo. The crude residue was purified by column chromatography (petroleum ether:EtOAc, 1:0 to 10:1) to give the title compound as an oil (47 mg, 33%).

Provenance & Evidence