Diethyl Ether → HCID 68688004, compound

Participants

Reaction Steps

To a solution of 10-(4-iodo-3-methylbenzoyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine of Step A (5.0 g, 0.0117 mmol) and N,N-diisopropylethylamine (3.25 mL, 0.0187 mol) in dry dichloromethane (50 mL) at room temperature under nitrogen was added dropwise trichloroacetyl chloride (1.95 mL, 0.0175 mol) and the reaction mixture was stirred at room temperature for 23 hours. Additional N,N-diisopropylethylamine (1.02 mL, 0.00583 mol) and trichloroacetyl chloride (0.65 mL, 0.00583 mol) were added and stirring continued at room temperature for 4 hours. The reaction mixture was then partitioned between dichloromethane (200 mL) and 2 M hydrochloric acid (200 mL). The organic phase was separated, washed with 2 M hydrochloric acid (200 mL) and water (200 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo to afford a black syrup. Purification by flash chromatography using a solvent gradient of 10 to 15% ethyl acetate in hexane gave an orange foam. Diethyl ether (100 mL) was added and the resulting suspension stirred vigorously for 4 hours then filtered to afford the title compound (5.21 g, 78%) as an off-white solid, m.p. 163° C.

Provenance & Evidence