Binap, (A+-)- → HCID 67417840, compound

Participants

Reaction Steps

A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (150 mg, 0.58 mmol), 4-(2-aminomethyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (187 mg, 0.64 mmol), Pd2(dba)3 (53 mg, 0.058 mmol), rac-BINAP (132 mg, 0.17 mmol) and NaOt-Bu (140 mg, 1.45 mmol) in DMA (6 mL) was heated at 80° C. for 1 h. The mixture was allowed to cool, diluted with EtOAc (25 mL) and washed with water (25 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated. Chromatography on silica (EtOAc/hexanes) yielded 4-{2-[(4-chloro-1-oxo-1,2-dihydro-phthalazin-6-ylamino)-methyl]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester. Deprotection with TFA in DCM yielded the title compound. 4-Chloro-6-(2-piperazin-1-yl-benzylamino)-2H-phthalazin-1-one: 46 mg (16.9%): m/z (M+H)=370.00. 1H-NMR (DMSO-d6) δ: 12.31 (s, 1H), 7.89 (d, 1H), 7.77 (m, 1H), 7.33 (d, 1H), 7.21 (m, 1H), 7.14 (dd, 1H), 7.10 (m, 1H), 7.00 (m, 1H), 6.64 (s, 1H), 4.43 (d, 2H), 2.90 (m, 5H), 2.82 (m, 4H).

Provenance & Evidence