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

Participants

Reaction Steps

To a solution of N-(2,6-difluoro-3-hydroxy-phenyl)-3-(3-fluorophenyl)-5-methoxy-benzamide (600 mg, 1.6 mmol, 1.0 eq) in THF under N2 was added dropwise a solution of BH3 (1M in THF, 8 mL, 8.0 mmol, 8.0 eq) at room temperature. The reaction mixture was heated at reflux for 4 h, then cooled and the reaction quenched by addition of 1M HCl. The aqueous layer was extracted with EtOAc and the combined organic extracts were washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo to give the product (550 mg, 95%) as yellow oil which was used directly to the next step without further purification.

Provenance & Evidence