2,5-Dimethoxybenzenemethanamine → 4-chloro-6-(2,5-dimethoxy-benzylamino)-2H-phthalazin-1-one

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Reaction Steps

A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (155 mg, 0.597 mmol), 2,5-dimethoxybenzylamine (0.096 mL, 0.636 mmol), Pd2(dba)3 (61 mg, 0.067 mmol), rac-BINAP (111 mg, 0.178 mmol) and NaOtBu (139 mg, 1.445 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-(2,5-dimethoxy-benzylamino)-2H-phthalazin-1-one (37 mg) as an off white solid, 1H (400 MHz, d6-DMSO) δ: 3.45 (s, 3H), 3.61 (s, 3H), 4.17 (d, 2H), 6.63 (m, 3H), 6.76 (d, 1H), 6.94 (dd, 1H), 7.33 (t, 1H), 7.72 (d, 1H), 12.14 (s, 1H) ppm; m/z (M+1) 345.92.

Provenance & Evidence