Boron tribromide → HCID 16038473, compound

Participants

Reaction Steps

To a solution of 10-[(2,2′-dimethyl-1,1′-biphenyl-4-yl)carbonyl]-N-(4-methoxybenzyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide of Example 8 (243 mg, 0.437 mmol) in dichloromethane (1.5 mL) at 0° C. under nitrogen was added a solution of boron tribromide in dichloromethane (1.0 M, 1.5 mL, 1.5 mmol) dropwise over 5 minutes. After 10 minutes at 0° C. the cooling bath was removed and the solution allowed to warm slowly to room temperature over 1.5 hours. The reaction was quenched by the addition of saturated aqueous sodium hydrogen carbonate solution (20 mL) and extracted with ethyl acetate (3×20 mL). The combined organic extracts were washed with a saturated aqueous sodium hydrogen carbonate solution (20 mL) and brine (20 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give a reddish oil (305 mg). Purification by flash chromatography using a solvent gradient of 0 to 2% methanol in dichloromethane gave the title compound (119 mg, 52%) as a white solid. MS [(+)ESI, m/z]: 542 [M+H]+.HRMS [(+)ESI, m/z]: 542.24405. Calcd for C35H32N3O3: 542.24437. Anal. Calcd for C35H31N3O3: C, 77.61; H, 5.77; N, 7.76. Found: C, 77.54; H, 5.79; N, 7.72.

Provenance & Evidence