Boron tribromide → HCID 178523484, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 5-(3-benzyloxy-phenyl)-1H-pyrazole-3-carboxylic acid {2-[4-(2-chloro-phenylamino)-piperidin-1-yl]-2-oxo-ethyl}-amide (0.19 g, 0.00035 mole) in dichloromethane was cooled to −70° C. 1 mL of a 1.6M solution of BBr3 in dichloromethane was then added dropwise with vigorous stirring. The reaction mixture was slowly brought to ambient temperature and stirring was continued at the same temperature for 1 hour. The reaction mixture was then cooled to −70° C. and ice cold water was added dropwise with stirring and while the mixture was slowly brought to ambient temperature. The product was extracted with dichloromethane and the organic layers were dried over sodium sulfate. The organic layer was collected and concentrated under reduced pressure. The resulting residue was recrystallized from ethyl acetate to afford 0.071 g (45%) of 5-(3-hydroxy-phenyl)-1H-pyrazole-3-carboxylic acid {2-[4-(2-chloro-phenylamino)-piperidin-1-yl]-2-oxo-ethyl}-amide. LCMS: 454.16 (M+1)+, 94.25%, 1H NMR (DMSO-d6): δ 13.6 (s, 1H), 9.6 (s, 1H), 8.1 (s, 1H), 7.0 (m, 5H), 6.84 (d, 1H), 6.76 (d, 1H), 6.6 (m, 1H), 4.8 (s, 1H), 4.3 (d, 1H), 4.1 (d, 2H), 3.8 (d, 1H), 3.7 (s, 1H), 3.2 (m, 1H), 2.8 (m, 1H), 1.95 (m, 2H), 1.3 (m, 2H).

Provenance & Evidence