2-(Azidomethyl)-6-(2,2,2-trifluoroethoxy)pyridine → [6-(2,2,2-Trifluoroethoxy)pyridin-2-yl]methanamine

A mixture of 2-(azidomethyl)-6-(2,2,2-trifluoroethoxy)pyridine (Step-5, 0.44 g, 1.90 mmol) and palladium 10% on carbon (0.070 g) in methanol (12 mL) is vigorously stirred at room temperature under hydrogen atmosphere (0.3 MPa) for 3 hours. After filtration through a pad of celite, the filtrate is concentrated in vacuo. The residue is diluted with methanol (4 mL) and applied onto a strong cation exchange cartridge (BondElute(registered trademark) SCX, 1 g/6 mL, Varian Inc.), and the solid phase matrix is rinsed with methanol (5 mL). The crude mixture is eluted with 1M ammonia in methanol (5 mL) and concentrated under reduced pressure to give 0.27 g (68% yield) of the title compound as dark brown oil.

1. filtrationAfter filtration through a pad of celite
2. concentrationthe filtrate is concentrated in vacuo
3. additionThe residue is diluted with methanol (4 mL)
4. wash), and the solid phase matrix is rinsed with methanol (5 mL)
5. washThe crude mixture is eluted with 1M ammonia in methanol (5 mL)
6. concentrationconcentrated under reduced pressure

ORD record

ord-07981e7ad62744beb74279f370a3a641

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09302991B2