Dichloromethane → 9-Chloro-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)-2,3-dihydro-1H-1,4-benzodiazepine

Participants

Reaction Conditions

Reaction Steps

Cesium carbonate (1.01 g, 3.08 mmol) was added to a solution of 2,2,2, -trifluoroethyl iodide (0.991 mL, 10.3 mmol) and 9-chloro-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepine (0.557 g, 2.06 mmol) in dimethylformamide. The reaction was heated at 50° C. for 96 h, adding more 2,2,2-trifluoroethyl iodide as needed. The reaction was worked up with methylene chloride and saturated brine. The residue was purified by chromatography (silica gel, 0–30% ethyl acetate in hexane gradient elution), giving the title compound (287 mg). 1H NMR (500 MHz, CDCl3) δ 7.66–7.23 (m, 8H), 5.20 (m, 1H), 4.85 (d, J=11 Hz, 1H), 4.24 (m, 1H), 3.79 (d, J=11 Hz, 1H).

Provenance & Evidence