2-Methoxyethylamine → 6-Bromo-N-(2-methoxyethyl)-3-pyridinemethanamine

To a solution of 6-bromonicotinaldehyde (7) (5 g, 26.9 mmol) in DCM (40 μL) was added 2-methoxyethylamine (8) (2.80 mL, 32.3 mmol). After 10 min, sodium triacetoxyborohydride (7.98 g, 37.6 mmol) was added to the mixture and the mixture was stirred at r.t. for 17 h. Additional amounts of DCM (100 mL), water (50 mL) and NH4Cl (50 mL) were added to the reaction mixture, which turned into a biphasic system. The organic phase was collected and the aqueous layer was extracted with DCM (3×100 μL). The combined organic solution were washed with brine, dried over anhydrous MgSO4 and concentrated under reduce pressure. The residue was purified by flash column chromatography (eluent a gradient DCM/MeOH from 98/2 to 95/5), to afford intermediate 9 (2.958 g, 45% yield) as a brown oil. MS (m/z): 245.1 (M+H).

1. customThe organic phase was collected
2. extractionthe aqueous layer was extracted with DCM (3×100 μL)
3. washThe combined organic solution were washed with brine
4. dry with materialdried over anhydrous MgSO4
5. concentrationconcentrated
6. customThe residue was purified by flash column chromatography (eluent a gradient DCM/MeOH from 98/2 to 95/5),

ORD record

ord-32a7270aa3d4438383a62c9b7ab9ae37

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08907091B2