Iodoethane → 6-(4-chlorophenyl)-4-ethyl-1-methyl-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-5(6H)-one

Participants

Reaction Steps

Into a 50 mL flask evacuated and brimmed with dry nitrogen, was charged with a solution of 6-(4-chlorophenyl)-1-methyl-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-5(6H)-one (Example 1, step 5; 100 mg, 0.31 mmol) in anhydrous tetrahydrofuran (10 mL). To this mixture, was added lithium bis(trimethylsilyl)amide (tetrahydrofuran solution) (0.17 mL, 0.33 mmol) at −78° C. The mixture was stirred at the same temperature for 1 hour, and then warmed to room temperature, maintained at the same temperature for 2 hours. Iodoethane (92.04 mg, 0.59 mmol) was added. The mixture was stirred at room temperature for another 2 hours. The reaction was quenched by ammonium chloride aqueous (5 mL), extracted with ethyl acetate (5 mL*3). The crude product was purified by column chromatography (silica gel, dichloromethane/methanol=25:1) to give 6-(4-chlorophenyl)-4-ethyl-1-methyl-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-5(6H)-one as a light yellow solid (20.0 mg, 18%). LRMS (M+H)+: calcd 352.11. found 352.

Provenance & Evidence