Binap, (A+-)- → HCID 24947782, compound

Participants

Reaction Steps

A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (204 mg, 0.785 mmol), N-(3-Aminomethyl-phenyl)-N′,N′-dimethyl-ethane-1,2-diamine hydrochloride (198 mg, 0.86 mmol), Pd2(dba)3 (72 mg, 0.0785 mmol), rac-BINAP (162 mg, 0.260 mmol) and NaOtBu (266 mg, 2.77 mmol) in DMA (6 mL) was heated at 85° C. for 3 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). Preparatory HPLC afforded 4-chloro-6-[3-(2-dimethylamino-ethylamino)-benzylamino]-2H-phthalazin-1-one hydroformate (81 mg) as a yellow solid. 1H (400 MHz, d6-DMSO) δ: 1.95 (s, 6H), 2.40 (m, 1H), 2.46 (m, 1H), 2.87 (m, 2H), 4.10 (d, 2H), 5.20 (bs, 1H), 6.26 (dd, 1H), 6.34 (d, 1H), 6.37 (s, 1H), 6.62 (s, 1H), 6.82 (t, 1H), 6.93 (dd, 1H), 7.40 (t, 1H), 7.70 (d, 1H), 7.95 (s, 1H), 12.12 (s, 1H) ppm; m/z (M+1) 372.04.

Provenance & Evidence