Binap, (A+-)- → 4-chloro-6-(2-morpholin-4-yl-benzylamino)-4a,8a-dihydro-2H-phthalazin-1-one

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Reaction Steps

A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (1.227 g, 4.728 mmol), (2-morpholino)benzylamine (1.00 g, 5.201 mmol), Pd2(dba)3 (450 mg, 0.491 mmol), rac-BINAP (883 mg, 1.418 mmol) and NaOtBu (1.17 g, 12.175 mmol) in DMA (20 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 (Hexanes/EtOAc) afforded 4-chloro-6-(2-morpholin-4-yl-benzylamino)-4a,8a-dihydro-2H-phthalazin-1-one (180 mg) as a white solid. 1H (400 MHz, d6-DMSO) δ: 2.90 (m, 4H), 3.79 (m, 4H), 4.46 (d, 2H), 6.66 (bs, 1H), 7.04 (t, 1H), 7.15 (m, 2H), 7.24 (m, 1H), 7.35 (d, 1H), 7.77 (t, 1H), 7.90 (d, 1H), 12.32 (s, 1H) ppm; m/z (M+1) 371.23.

Provenance & Evidence