Cesium carbonate → 6-(4-Chlorophenyl)-1-methyl-5,6-dihydrospiro[benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine-4,1'-cyclopropane]

Participants

Reaction Steps

A solution of 1-methyl-5,6-dihydrospiro[benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine-4,1′-cyclopropane] (111 mg, 0.49 mmol), 1-chloro-4-iodobenzene (468 mg, 2.0 mmol), tris(dibenzylideneacetone)dipalladium(0) (35 mg, 0.049 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (40 mg, 0.098 mmol) and cesium carbonate anhydrous (320 mg, 0.98 mmol) in toluene (10 mL) was heated to 110° C., and maintained at the same temperature for 12 hours. The reaction mixture was concentrated, added with water (20 mL), extracted with ethyl acetate (20 mL). The organic phase was separated, and concentrated to give a crude product, which was purified by preparative-TLC (silica-gel, dichloromethane/methanol=30:1) to afford 6-(4-chlorophenyl)-1-methyl-5,6-dihydrospiro[benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine-4,1′-cyclopropane] (8 mg, 4.8%).

Provenance & Evidence