2-Methoxyethylamine → N-((6-Bromopyridin-2-yl)methyl)-2-methoxyethanamine

Participants

Reaction Steps

A mixture of 6-bromo-2-pyridinecarboxaldehyde (54) (20 g, 108 mmol) and 2-methoxy ethanamine (10.3 mL, 8.88 g, 118 mmol) in DCM (1.3 L) was stirred at room temperature for 10 min. It was then treated with NaBH(OAc)3 (25 g, 118 mmol) and stirred at room temperature overnight. The reaction mixture was quenched with water (400 mL) and acidified to pH=4 with 1M HCl (−140 mL). The two phases were separated and the organic layer was extracted with 0.25M HCl (2×500 mL). The aqueous layers were combined, basified to pH=9 with 4N NaOH, extracted with DCM (1×500 mL), dried over Na2SO4, filtered and concentrated yielding 25.2 g of 55 (96%). MS (m/z): 245.1 (M+1).

Provenance & Evidence