(3,5-Dimethoxyphenyl)methanamine → HCID 24948720, compound

Participants

Reaction Steps

A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (105 mg, 0.405 mmol), 3,5-dimethoxybenzylamine (0.64 mL, 0.424 mmol), Pd2(dba)3 (25 mg, 0.027 mmol), rac-BINAP (78 mg, 0.125 mmol) and NaOt-Bu (92 mg, 0.963 mmol) in DMA (6 mL) was heated at 80° 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-(3,5-dimethoxy-benzylamino)-2H-phthalazin-1-one (3 mg) as a brown solid, 1H (400 MHz, CDCl3) δ: 3.65 (d, 6H), 4.28 (s, 2H), 6.25 (m, 1H), 6.42 (m, 2H), 6.81 (m, 1H), 6.95 (m, 2H), 8.00 (m, 1H), ppm. m/z (M+1) 345.92.

Provenance & Evidence