Diethyl Ether → HCID 15952275, compound

Participants

Reaction Steps

To a solution of 10-[(2′-formyl-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 56 (0.132 g, 0.251 mmol) in dry tetrahydrofuran (15 mL) was added 3.0 Methylmagnesium bromide in diethyl ether (0.68 mL, 2.04 mmol) and the reaction mixture stirred at room temperature under nitrogen for 17 hours. The reaction was quenched by the addition of saturated aqueous ammonium chloride solution (20 mL) and then the mixture partitioned between ethyl acetate (100 mL) and half saturated aqueous ammonium chloride solution (100 mL). The organic phase was separated, washed with brine (100 ml), dried over anhydrous magnesium sulfate, and concentrated in vacuo to afford a cream foam. Purification by flash chromatography using a solvent gradient of 1 to 6% methanol in dichloromethane gave a colorless glass that was triturated with diethyl ether to afford the title compound (0.039 g, 28%) as a white solid, m.p. 111-115° C.

Provenance & Evidence