Acetic Acid → 6-Bromo-N-(2-methoxyethyl)-3-pyridinemethanamine

To a dark-yellow solution of 6-bromopyridine-3-carbaldehyde 7 (30 g, 161 mmol) in DCM (300 ml) and 2-methoxyethylamine 8 (1.05 eq, 14.72 ml, 169 mmol) in a 1 L round-bottom flask was added acetic acid (1 eq, 9.23 mL, 161 mmol). After 15 min, sodium triacetoxyborohydride (1.05 eq, 35.9 g, 169 mmol) was added over 10 min and the reaction mixture was stirred at r.t. for 30 min. The reaction mixture was then quenched with 10% HCl (200 mL). The two layers were separated and the organic layer was extracted with 10% HCl (2×100 mL). The aqueous layers were combined, basified to pH=9 with 4M NaOH (450 mL), extracted with EA (3×150 mL) and combined organic extracts were washed with brine (150 mL), dried over Na2SO4, filtered and evaporated to afford 9 as brown oil that could be used crude for next step (31.1 g, 127 mmol, 79% yield). MS (m/z): 245.1 (M+1)

1. customThe reaction mixture was then quenched with 10% HCl (200 mL)
2. customThe two layers were separated
3. extractionthe organic layer was extracted with 10% HCl (2×100 mL)
4. extractionextracted with EA (3×150 mL)
5. washwere washed with brine (150 mL)
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. customevaporated

ORD record

ord-197a1e467fda4221962d42460bae6321

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09018378B2