Water → 3-Nitro-2-(tetrahydro-2H-pyran-4-yloxy)pyridine

Temperatur

0 °C

To a stirred solution of tetrahydro-2H-pyran-4-ol (2.5 g, 24.5 mmol) in anhydrous THF (20 mL) at 0° C. was added sodium hydride (60% dispersion in oil, 0.938 g, 24.5 mmol) and the mixture stirred at 0° C. for 0.5 h. A solution of 2-fluoro-3-nitro-pyridine (3.3 g, 23.2 mmol) in anhydrous THF (5 mL) was added drop wise with stirring and the solution allowed to warm to ambient temperature over 5 hours. The reaction was cooled in an ice-bath and water (50 mL) added. The mixture was extracted with EtOAc (2×100 mL) and the combined organic layers washed with brine (50 mL), dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified flash column chromatography (20% iso-hexane/DCM DCM) to yield the title compound as pale yellow oil (2.67 g, 48% yield).

1. stirringwith stirring
2. temperatureto warm to ambient temperature over 5 hours
3. temperatureThe reaction was cooled in an ice-bath
4. extractionThe mixture was extracted with EtOAc (2×100 mL)
5. washthe combined organic layers washed with brine (50 mL)
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe crude product was purified flash column chromatography (20% iso-hexane/DCM DCM)

ORD-Eintrag

ord-21fabf6e02d24cf8b7769255a7d27cfb

Quelldatensatz

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08486953B2