Binap, (A+-)- → 4-{2-[(4-Chloro-1-oxo-1,2-dihydro-phthalazin-6-ylamino)-methyl]-4-trifluoromethyl-phenyl}-piperazine-1-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-bromo-4-chloro-2H-phthalazin-1-one (183 mg, 0.70 mmol), 4-(2-aminomethyl-4-trifluoromethyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (230 mg, 0.64 mmol), Pd2(dba)3 (59 mg, 0.064 mmol), BINAP (120 mg, 0.19 mmol) and NaOt-Bu (180 mg, 1.92 mmol) in DMA (10 mL) was purged with nitrogen for 10 min. The mixture was heated at 90° C. for 5 h. The mixture was allowed to cool and diluted with ethyl acetate (30 mL) and washed with ammonium chloride (25 mL). The organic layer was dried and concentrated. Chromatography on silica yielded the title compound (25 mg) m/z (M+H)=538.90.

Provenance & Evidence