Binap, (A+-)- → 4-((2,6-dimethylpyridin-3-yl)methylamino)-2-methyl-6-(((1S,2S)-2-(pyridin-2-yl)cyclopropyl)methoxy)pyridazin-3(2H)-one

Participants

Reaction Conditions

Reaction Steps

A mixture of (2,6-dimethylpyridin-3-yl)methanamine (30 mg, 0.2 mmol), 4-bromo-2-methyl-6-(((1S,2S)-2-(pyridin-2-yl)cyclopropyl)methoxy)pyridazin-3(2H)-one (68 mg, 0.2 mmol), Pd2(dba)3 (18 mg, 0.02 mmol), BINAP (18 mg, 0.03 mmol) and t-BuONa (38 mg, 0.4 mmol) in toluene (4 mL) under N2 was heated at 80° C. for 4 h. The mixture was filtered and concentrated to give crude product which was purified by Prep-HPLC to give the title compound as oil. 1H NMR (400 MHz, CD3OD) δ 8.34 (d, 1H), 7.67-7.62 (m, 1H), 7.47 (d, 1H), 7.21 (d, 1H), 7.16-7.13 (m, 1H), 7.05 (d, 1H), 5.67 (s, 1H), 4.35 (s, 2H), 4.20-4.16 (m, 1H), 4.03-3.98 (m, 1H), 3.63 (s, 3H), 2.50 (s, 3H), 2.46 (s, 3H), 2.11-2.07 (m, 1H), 1.84-1.79 (m, 1H), 1.26-1.21 (m, 1H), 1.09-1.04 (m, 1H), LCMS m/z (M+H) 392.2 found, 392.2 required.

Provenance & Evidence