Boron tribromide → HCID 66689542, compound

Participants

Reaction Steps

To a suspension of the 4-tert-butyl-N-{1-[3-(4-methoxyphenyl)-4-oxo-3,4-dihydroquinazolin-2-yl]ethyl}-N-methylbenzenesulfonamide (0.5 g, 1.07 mmol) stirring in 15 mL DCM was added boron tribromide (5 mL, 5 mmol 1M in DCM). The reaction was allowed to stir at room temperature for 15 min after which TLC analysis indicated that starting material was completely consumed. The reaction was quenched with 20 mL brine and the resulting mixture was transferred to a separatory funnel. The layers were separated and the aqueous layer extracted with CHCl3 (2×25 mL). The combined organics were washed with brine, dried over MgSO4, and concentrated under vacuum to afford a crude residue that was purified by chromatography (silica gel, 0-75% EtOAc:Hex), yielding the desired product as a white solid (0.735 g, 95%). 1H-NMR (CDCl3): δ 8.26 (d, 1H), 7.67 (t, 1H), 7.51 (d, 2H), 7.45 (t, 1H), 7.36 (m, 2H), 7.26 (d, 2H), 6.98 (m, 1H), 6.90 (m, 2H), 5.00 (q, 1H), 3.19 (s, 3H), 1.28 (d, 3H), 1.17 (s, 9H); MS (ESI) 492 (MH+).

Provenance & Evidence