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

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).

1. stirringstirred at room temperature overnight
2. customThe reaction mixture was quenched with water (400 mL)
3. customThe two phases were separated
4. extractionthe organic layer was extracted with 0.25M HCl (2×500 mL)
5. extractionextracted with DCM (1×500 mL)
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-d979361bede54acd906d8e190553509e

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09018378B2