Methyl iodide → 6-(4-chlorophenyl)-1,4-dimethyl-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-5(6H)-one

Participants

Reaction Steps

To a solution of 6-(4-chlorophenyl)-1-methyl-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-5(6H)-one (100 mg, 0.31 mmol) in THF was added LiHMDS (0.17 mL, 0.33 mmol) at −78° C. The mixture was stirred at the same temperature for 1 h, and then CH3I (84.00 mg, 0.59 mmol) was added. The mixture was stirred at −78° C. for 2 h, then warmed to room temperature, and maintained at room temperature for 2 h. NH4Cl aqueous (15 mL) was added, and then extracted with DCM (10 mL*3). The product was purified by column chromatography (silica-gel, DCM:MEOH=30:1) to give 6-(4-chlorophenyl)-1,4-dimethyl-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-5(6H)-one (40.0 mg, 38%). LRMS (M+H+) m/z: calcd 338.09. found 338.

Provenance & Evidence