Diphenylmethylidenehydrazine → N-benzhydrylidene-N'-isoquinolin-5-yl-hydrazine

Participants

Reaction Conditions

Reaction Steps

To a suspension of 5-bromoisoquinoline (200 mg, 0.96 mmol), benzhydrylidene-hydrazine (189 mg, 0.96 mmol), palladium diacetate (2.2 mg, 0.0096 mmol) and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP, 6 mg, 0.0096 mmol) in dry toluene (1 mL), sodium tert-butoxide (130 mg, 1.34 mmol) was added and the mixture was heated at 85° C. for 4 hours. The mixture, cooled to room temperature, was filtered over celite and the pad was washed with diethylether. The solvent was evaporated under vacuum and the residue was purified by flash chromatography with hexane/ethylacetate 7/3 as eluant, affording 268 mg of the title compound (86% yield).

Provenance & Evidence