Boron tribromide → HCID 44124905, compound

Participants

Reaction Steps

To a stirred solution of compound from Example 39 (770 mg, 1.52 mmol) in 14 mL of DCM at −78° C. was added a solution of BBr3 (4.58 mmol) in DCM. After 1 hour, the reaction mixture was warned up to −25° C. and the reaction was monitored by TLC. After completion, the mixture was quenched with sat. NaHCO3. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (3×100 mL). The combinated organic layer were washed with brine, dried over MgSO4 and concentrated to gave the crude product, which was purified by a flash column chromatography give 172 mg of the title compound (0.351 mmol, 23%): 1H NMR (400 MHz, CD3OD): δ 8.63 (s, 1H), 7.89 (s, 1H), 7.20-7.15 (m, 3H), 4.83-4.79 (m, 2H), 4.15-3.85 (m, 2H), 3.81-3.60 (m, 2H), 3.40 (s, 2H), 3.35 (s, 3H), 3.30-3.00 (m, 3H), 2.80-2.60 (m, 3H), 2.32-2.20 (m, 1H), 2.10-1.99 (m, 1H); MS (ESI) m/z: Calculated for C24H25F3N4O4: 490.47. found 491.1 (M+H)+.

Provenance & Evidence