Water → 4-fluoro-2-hydroxy-N-[2-[2-[[3-(trifluoromethyl)phenyl]sulfonyl]-ethylsulfanyl]-pyridin-3-yl]benzamide

Participants

Reaction Conditions

Reaction Steps

A solution of 515 mg (1.0 mmol) 4-fluoro-2-methoxy-N-[2-[2-[[3-(trifluoromethyl)phenyl]sulfonyl]-ethylsulfanyl]-pyridin-3-yl]benzamide (example compound 50) in DCM (5 ml) was cooled to −78° C. 5 ml (1 M in DCM, 5.0 mmol) BBr3 were added at this temperature and the mixture was stirred for 1 h at −78° C. Then the reaction solution was poured into an iced water mixture and it was adjusted to pH 8 with NaHCO3. Then it was extracted with DCM and the organic phase was washed with water and brine, dried over Na2SO4, filtered and concentrated to small volume under vacuum. 290 mg of 4-fluoro-2-hydroxy-N-[2-[2-[[3-(trifluoromethyl)phenyl]sulfonyl]-ethylsulfanyl]-pyridin-3-yl]benzamide were obtained as residue. MS: m/z 501.0 [M+H]+.

Provenance & Evidence