Boron tribromide → HCID 136499144, compound

Participants

Reaction Steps

To a stirred solution of 5-[3-fluoro-2′-methoxy-4′-(trifluoromethyl)biphenyl-4-yl]pyrazin-2-amine (370 mg, 1.02 mmol) in dry dichloromethane (9.8 mL) at −78° Celsius, was added a boron tribromide in dichloromethane (3.1 mL, 1 M). The flask was slowly warmed to rt and stirred overnight. The reaction was poured into sat. NH4Cl and the pH adjusted to 8 with saturated NaHCO3. The resultant mixture was extracted with DCM (3×30 mL) and the combined extracts dried over Na2SO4, filtered and concentrated to dryness. The crude product was purified by HPLC to give the title compound. MS (ESI): mass calcd. for C17H11F4N3O, 349.08; m/z found, 350.1 [M+H]+. 1H NMR (500 MHz, CD3OD) δ 8.41-8.35 (m, 1H), 8.17-8.10 (d, J=1.5, 1H), 7.99-7.88 (m, 1H), 7.56-7.46 (m, 3H), 7.22-7.19 (m, 1H), 7.19-7.17 (d, J=1.7, 1H).

Provenance & Evidence