Borane;tetrahydrofuran → HCID 58476618, compound

Temperature

50 °C

To a solution of 3-(5-bromo-2-methoxypyridin-3-yl)-N,N-dimethylpropanamide (1.0 g, 3.0 mmol) in THF (40 mL) was added borane-tetrahydrofuran (1.0 M in THF, 8.71 mL) slowly. The reaction mixture was allowed to stir for 3 h at 50° C. The mixture was allowed to cool to rt and then concentrated to dryness. To the residue, a solution of HCl (3.0 M in water, 40 mL) was added. The resulting mixture was allowed to stir for 2 h at 80° C. The mixture was allowed to cool to rt and then was basified to pH>10 with a potassium hydroxide solution. The aqueous solution was extracted with DCM. The organic solutions were combined, washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give 3-(5-bromo-2-methoxypyridin-3-yl)-N,N-dimethylpropan-1-amine (0.377 g, 40%) as an oil. LCMS (FA): Rt=1.03 min, m/z=273.1 (M+H).

1. temperatureto cool to rt
2. concentrationconcentrated to dryness
3. additionTo the residue, a solution of HCl (3.0 M in water, 40 mL) was added
4. stirringto stir for 2 h at 80° C
5. temperatureto cool to rt
6. extractionThe aqueous solution was extracted with DCM
7. washwashed with brine
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated
11. customThe residue was purified by column chromatography

ORD record

ord-01abe5fc45f7419f99c455241e516001

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08268992B2