Methanol → 2-Bromo-6-methoxypyridine

Dried sodium (970 mg, 42.2 mmol) was added portionwise to cooled methanol (50 ml) under nitrogen, and once addition was complete, 2,6-dibromopyridine (10 g, 42.2 mmol) was added portionwise. The resulting suspension was heated under reflux for 24 hours. The cooled reaction was concentrated under reduced pressure, the residue diluted with water (100 ml), and extracted with ethyl acetate (2×75 ml). The organic extracts were dried (MgSO4), and evaporated under reduced pressure to give a pale yellow oil. The crude product was purified by column chromatography on silica gel using an elution gradient of pentane:ethyl acetate (100:0 to 98:2) to give the title compound as a clear oil, 4.23 g.

1. additiononce addition
2. temperatureThe resulting suspension was heated
3. temperatureunder reflux for 24 hours
4. customThe cooled reaction
5. concentrationwas concentrated under reduced pressure
6. additionthe residue diluted with water (100 ml)
7. extractionextracted with ethyl acetate (2×75 ml)
8. dry with materialThe organic extracts were dried (MgSO4)
9. customevaporated under reduced pressure
10. customto give a pale yellow oil
11. customThe crude product was purified by column chromatography on silica gel using an elution gradient of pentane:ethyl acetate (100:0 to 98:2)

ORD record

ord-23ed7afed8ae451e800d71d8a07e953f

Source dataset

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07060836B2