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

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Reaction Steps

A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (148 mg, 0.570 mmol), 2-imidazol-1-yl-benzylamine (110 mg, 0.635 mmol), Pd2(dba)3 (53 mg, 0.0578 mmol), rac-BINAP (117 mg, 0.188 mmol) and NaOtBu (227 mg, 2.362 mmol) in DMA (5 mL) was heated at 85° C. for 45 minutes. 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-imidazol-1-yl-benzylamino)-2H-phthalazin-1-one (17 mg) as a yellow solid, 1H (400 MHz, d6-DMSO) δ: 4.24 (d, 2H), 6.64 (s, 1H), 7.06 (dd, 1H), 7.11 (s, 1H), 7.41 (m, 1H), 7.46 (m, 2H), 7.52 (m, 2H), 7.59 (t, 1H), 7.92 (m, 2H), 12.36 (1H) ppm; m/z (M+1) 351.99.

Provenance & Evidence