Isopropanol → 2-(1-Methylethoxy)-3-nitropyridine

iso-Propanol (1.41 mL, 18.48 mmol) was added drop wise into a stirred suspension of sodium hydride (60% dispersion in oil, 0.739 g, 18.48 mmol) in anhydrous THF (20 mL) at 0° C. and the resulting solution stirred for 0.5 hours. To this solution was added 2-fluoro-3-nitropyridine (2.50 g, 17.60 mmol) drop wise in anhydrous THF (10 mL). After complete addition the solution was stirred at 0° C. for 0.5 hours, before being allowed to warm to ambient temperature. The reaction was stirred at ambient temperature for 18 hours, quenched with water (50 mL) and the aqueous layer extracted with diethyl ether (3×50 mL). The organic layers were combined, washed with brine (50 mL), dried (Na2SO4), filtered and concentrated in vacuo. The title compound was obtained as a yellow solid (1.975 g, 61% yield) after purification by flash-column chromatography (petroleum ether (40-60° C.)/DCM).

1. additionAfter complete addition the solution
2. stirringwas stirred at 0° C. for 0.5 hours
3. stirringThe reaction was stirred at ambient temperature for 18 hours
4. customquenched with water (50 mL)
5. extractionthe aqueous layer extracted with diethyl ether (3×50 mL)
6. washwashed with brine (50 mL)
7. dry with materialdried (Na2SO4)
8. filtrationfiltered
9. concentrationconcentrated in vacuo

ORD record

ord-65dea844765a4f67adfebf05203fa3e9

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08486953B2