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

To a solution of 6-bromonicotinaldehyde (7) (5 g, 26.9 mmol) in DCM (40 mL) 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 mL). 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). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.31 (dd, J=2.6, 0.6 Hz, 1H), 7.70 (dd, J=8.2, 2.6 Hz, 1H), 7.58 (d, J=8.4 Hz, 1H), 3.69 (s, 2H), 3.37 (t, J=5.8 Hz, 2H), 3.22 (s, 3H), 2.60 (t, J=5.8 Hz, 2H).

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

ORD record

ord-33e3c651b9c84691949ae115f4b8a05b

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08569503B2