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

To a solution of 6-bromopyridine-3-carbaldehyde (5 g, 26.9 mmol) in DCM (40 mL). was added 2-methoxyethylamine (2.80 mL, 32.3 mmol). After 10 min, sodium triacetoxyborohydride (7.98 g, 37.6 mmol) was added to the mixture and it was stirred at r.t for 17 h. DCM (100 mL water (50 mL and NH4Cl (50 mL) were added to the reaction mixture. The organic phase was collected and the aqueous layer was extracted with DCM (3×100 mL). The combined organic solutions were washed with brine and concentrated under reduce pressure. The residue was purified by flash column chromatography, eluent 98/2 to 95/5 DCM/MeOH, to afford title 143 (2.958 g, 45% yield) as a brown oil. 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). MS (m/z): 245.1 (M+H).

1. customThe organic phase was collected
2. extractionthe aqueous layer was extracted with DCM (3×100 mL)
3. washThe combined organic solutions were washed with brine
4. concentrationconcentrated
5. customThe residue was purified by flash column chromatography, eluent 98/2 to 95/5 DCM/MeOH

ORD record

ord-f9b5fff668e7412db66bc860204a1a9e

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08759522B2