Benzyl Alcohol → HCID 68687595, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of benzylalcohol (0.025 mL, 0.241 mmol) in dry tetrahydrofuran (5 mL) at 0° C. under nitrogen was added a 1.0 M solution of sodium bis(trimethylsilyl)amide in tetrahydrofuran (0.26 mL, 0.26 mmol) and the reaction mixture stirred at 0° C. for 20 minutes. A solution of 10-[(6-chloropyridin-3-yl)carbonyl]-N-(pyridin-3-ylmethyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide of Example 117 (0.100 g, 0.219 mmol) in dry tetrahydrofuran (5 mL) was added and the reaction mixture was stirred at room temperature for 72 hours. The reaction was quenched by the addition of saturated aqueous ammonium chloride solution (10 mL) and then diluted with ethyl acetate (10 mL). The organic phase was separated, washed with water (10 mL) and brine (10 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo to afford a yellow oil. Purification by flash chromatography using a solvent gradient of 0 to 4% methanol in dichloromethane gave a white foam that was triturated with diethyl ether to afford the title compound (0.034 g, 30%) as a white solid.

Provenance & Evidence