Binap, (A+-)- → 4-Chloro-6-(5-chloro-2-methyl-benzylamino)-2H-phthalazin-1-one

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Reaction Steps

A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (150 mg, 0.58 mmol), 5-chloro-2-methyl-benzylamine (100 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 the title compound. 4-Chloro-6-(5-chloro-2-methyl-benzylamino)-2H-phthalazin-1-one: 20 mg (10.3%): m/z (M+H)=334. 1H-NMR (DMSO-d6) δ: 12.63 (s, 1H), 8.21 (d, 1H), 7.78 (m, 1H), 7.56 (m, 1H), 7.50 (m, 2H), 7.42 (dd, 1H), 7.10 (s, 1H), 4.66 (d, 2H), 2.60 (s, 3H).

Provenance & Evidence