Diethyl Ether → 1-(6-Chloropyridin-3-yl)propan-1-one

Temperature

25 °C

To a solution of 6-chloro-N-methoxy-N-methyl nicotinamide (6.0 g, 30 mmol) (produced as disclosed in Perner, R. J. J. Med. Chem. 2003, 46, 5249) in THF (100 mL) was added a 3M solution of ethyl magnesium chloride in ether (15 mL, 45 mmol). The reaction mixture was heated under reflux for 4 hours and then stirred at approximately 25° C. for 14 hours. The reaction mixture was treated with a saturated aqueous solution of ammonium chloride (100 mL) and then extracted with ethyl acetate (2×100 mL). The combined extracts were washed with brine, dried (Na2SO4) and concentrated. The residue was purified by chromatography over silica gel, eluting with 10 percent ethyl acetate in hexane to give product as a white solid. (2.8 g, 60 percent yield).

1. temperatureThe reaction mixture was heated
2. temperatureunder reflux for 4 hours
3. extractionextracted with ethyl acetate (2×100 mL)
4. washThe combined extracts were washed with brine
5. dry with materialdried (Na2SO4)
6. concentrationconcentrated
7. customThe residue was purified by chromatography over silica gel
8. washeluting with 10 percent ethyl acetate in hexane
9. customto give product as a white solid

ORD record

ord-6502138605bb400b84e2243b5c984ab7

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08008487B2