Binap, (A+-)- → 4-chloro-6-(2,3-difluoro-benzylamino)-2H-phthalazin-1-one

Participants

Reaction Steps

A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (156 mg, 0.601 mmol), 2,3-difluorobenzylamine (0.074 mL, 0.646 mmol), Pd2(dba)3 (53 mg, 0.058 mmol), rac-BINAP (104 mg, 0.167 mmol) and NaOtBu (134 mg, 1.39 mmol) in DMA (6 mL) was heated at 80° C. for 1.5 h. The mixture was allowed to cool, diluted with EtOAc and washed with water. The organic layer was washed with sat.aq. NaHCO3, brine and dried (Na2SO4). Chromatography on silica (EtOAc/hexanes) afforded 4-chloro-6-(2,3-difluoro-benzylamino)-2H-phthalazin-1-one (27 mg) as an off white solid, 1H (400 MHz, CDCl3) δ: 4.45 (s, 2H), 6.84 (d, 1H), 6.96 (m, 2H), 7.03 (m, 2H), 8.01 (d, 1H), 11.00 (s, 1H) ppm; m/z (M+1) 321.91.

Provenance & Evidence