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

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(2,6-difluoro-3-hydroxy-phenyl)-5-(3,5-difluorophenyl)-2,3-dimethyl-benzamide (46 mg, 0.12 mmol, 1.0 eq) in THF (5 mL) under N2 was added dropwise a solution of BH3 (1M in THF, 0.72 mL, 0.72 mmol, 6.0 eq). The reaction mixture was heated at 60° C. overnight. After cooling, the resulting mixture was quenched with water and extracted with EtOAc. The organic extract was washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by column chromatography (petroleum ether:EtOAc, 40:1 to 20:1) to give the title compound as a colorless oil (20 mg, 45%).

Provenance & Evidence