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

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Reaction Steps

A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (150 mg, 0.578 mmol), [3-(morpholinomethyl)phenyl]methylamine (131 mg, 0.636 mmol), Pd2(dba)3 (53 mg, 0.0578 mmol), rac-BINAP (108 mg, 0.173 mmol) and NaOtBu (139 mg, 1.445 mmol) in DMA (5 mL) was heated at 85° C. for 1 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-(3-morpholin-4-ylmethyl-benzylamino)-2H-phthalazin-1-one (42 mg) as an off white solid, 1H (400 MHz, d6-DMSO) δ: 2.11 (m, 4H), 3.23 (s, 2H), 3.30 (t, 4H), 4.25 (d, 2H), 6.60 (s, 1H), 6.98 (m, 2H), 7.10 (m, 3H), 7.50 (t, 1H), 7.74 (d, 1H), 12.16 (s, 1H) ppm; m/z (M+1) 384.94.

Provenance & Evidence