Boron tribromide → 2-chloro-4-((1R,2S)-1-(5-(4-cyanophenyl)-1,3,4-oxadiazol-2-yl)-3,3,3-trifluoro-2-hydroxypropylamino)-3-methylbenzonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-((1R,2S)-2-(benzyloxy)-1-(5-(4-cyanophenyl)-1,3,4-oxadiazol-2-yl)-3,3,3-trifluoropropylamino)-2-chloro-3-methylbenzonitrile (170 mg, 0.32 mmol) in DCM (15 mL) was added BBr3 (380 mg, 1.52 mmol) in 0.7 mL DCM at 0° C. The reaction mixture was stirred at 0° C. for 2 h until the starting material completely disappeared. The reaction was quenched with saturated aq. NaHCO3 solution, extracted with EtOAc. The EtOAc extracts were washed with water, brine and dried over Na2SO4. After the solvent was removed, the residue was purified by flash chromatography to provide the title compound 2-chloro-4-((1R,2S)-1-(5-(4-cyanophenyl)-1,3,4-oxadiazol-2-yl)-3,3,3-trifluoro-2-hydroxypropylamino)-3-methylbenzonitrile (74.6 mg, 53%) as a white solid. 1H NMR (400 MHz, Acetone-d6, δ in ppm) 8.23 (d, J=8.6 Hz, 2H), 8.01 (d, J=8.6 Hz, 2H), 7.55 (d, J=8.6 Hz, 1H), 7.06 (d, J=8.6 Hz, 1H), 6.73 (b, 1H), 5.77 (d, J=9.4 Hz, 1H), 5.72 (dd, J=2.4, 9.0 Hz, 1H), 5.21 (m, 1H), 2.40 (s, 3H).

Provenance & Evidence