Boron tribromide → HCID 15951892, compound

Participants

Reaction Steps

To a suspension of 10-[(2′-ethoxy-1,1′-biphenyl-4-yl)carbonyl]-N-(pyridin-3-ylmethyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide of Example 33 (0.281 g, 0.518 mmol) in dry dichloromethane (2.6 mL) at 0° C. under nitrogen was added dropwise a 1.0 M solution of boron tribromide in dichloromethane (2.6 mL, 2.6 mmol) over ca. 5 minutes. The reaction mixture was allowed to warm to room temperature and then stirred for 5 hours. The reaction was quenched by the addition of saturated aqueous sodium bicarbonate solution (50 mL) and extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with brine (50 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo to give a tan solid (0.210 g). Purification by flash chromatography using a solvent gradient of 1 to 4% methanol in dichloromethane gave the title compound (0.042 g, 16%) as a white solid.

Provenance & Evidence