Boron tribromide → HCID 66605886, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4-(3-bromo-4-fluorophenyl)-3-{4-[(3-methoxypropyl)amino]-1,2,5-oxadiazol-3-yl}-1,2,4-oxadiazol-5(4H)-one (6.3 g, 14 mmol) in dichloromethane (60 mL) at −78° C. was treated with 1M boron tribromide in dichloromethane (28 mL, 28 mmol) and stirred at 25° C. for 2 h. The reaction mixture was cooled to 0° C. and quenched with saturated sodium bicarbonate (100 mL). The aqueous layer was separated and extracted with dichloromethane (2×150 mL). The combined organic layers were washed with brine (100 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to a crude off-white solid. This material was purified on silica gel to give the desired product (4.0 g, 73%) as a white solid. LCMS for C13H12BrFN5O4 (M+H)+: m/z=400.0, 402.0. 1H NMR (400 MHz, DMSO-d6): δ 8.07 (dd, J=6.2, 2.5 Hz, 1 H), 7.72-7.68 (m, 1 H), 7.59 (dd, J=8.8, 8.6 Hz, 1 H), 6.54 (t, J=5.7 Hz, 1 H), 4.60 (t, J=5.1 Hz, 1 H), 3.48-3.43 (m, 2 H), 3.32-3.26 (m, 2 H), 1.74-1.67 (m, 2 H).

Provenance & Evidence