Diphenylmethylidenehydrazine → HCID 86653535, compound

Participants

Reaction Steps

5-Bromo-2(1H)-pyridone (2.0 g, 11.5 mmol) in 25 mL dry toluene was treated with benzophenone hydrazone (2.50 g, 12.7 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (200 mg, 0.345 mmol), and sodium tert-butoxide (2.2 g, 23 mmol). The mixture was degassed with argon for 15 minutes. Added Pd(II)(OAc)2 (80 mg, 0.345 mmol) and stirred at 90° C. for 16 hours. Extracted using EtOAc/H2O (3×150 mL EtOAc, 1×150 mL brine). Dried using Na2SO4 and then purified by flash chromatography (silica, 0-12% MeOH/DCM) to afford 5-(2-(diphenylmethylene)hydrazinyl)pyridin-2(1H)-one (950 mg, 3.28 mmol, 29%). 1H NMR (300 MHz, DMSO-d6) δ 11.12 (s, 1H), 8.49 (s, 1H), 7.61-7.25 (m, 12H), 6.31 (d, 1H); LC-MS (ESI) m/z 290 (M+H)+.

Provenance & Evidence