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

Participants

Reaction Steps

A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (150 mg, 0.578 mmol), 2-(trifluoromethoxy)benzylamine (122 mg, 0.636 mmol), Pd2(dba)3 (49 mg, 0.0535 mmol), rac-BINAP (104 mg, 0.167 mmol) and NaOtBu (142 mg, 1.478 mmol) in DMA (5 mL) was heated at 85° 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-trifluoromethoxy-benzylamino)-2H-phthalazin-1-one (41 mg) as a beige solid, 1H (400 MHz, d6-DMSO) δ: 4.50 (s, 2H), 6.78 (s, 1H), 7.16 (dd, 1H), 7.40 (m, 3H), 7.47 (d, 1H), 7.68 (t, 1H) m 7.95 (d, 1H), 12.37 (s, 1H) ppm; m/z (M+1) 369.86.

Provenance & Evidence