2,4-Difluoroaniline → 8-(2,4-difluorophenyl)-3-(2,4-difluorophenylamino)-1-methylpyrido[3,2-d]pyridazin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

To a suspension of 3-bromo-8-(2,4-difluorophenyl)-1-methylpyrido[3,2-d]pyridazin-2(1H)-one (8) (60.0 mg, 0.170 mmol) in toluene (2 mL) was added palladium (II) acetate (1.91 mg, 0.00852 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos) (9.86 mg, 0.0170 mmol) and cesium carbonate (83.3 mg, 0.256 mmol) followed by 2,4-difluorobenzenamine (0.0260 mL, 0.256 mmol). The reaction mixture was stirred and heated in a microwave at 110° C. for 75 min and then cooled to RT to afford a suspension. The solid was collected by suction filtration, washed with toluene and water, and dried in vacuo to give 8-(2,4-difluorophenyl)-3-(2,4-difluorophenylamino)-1-methylpyrido[3,2-d]pyridazin-2(1H)-one as a pale yellow solid. MS (ESI, pos. ion) m/z: 401 (M+1).

Provenance & Evidence