Water → 3-Bromo-5-[(pyridin-3-yl)oxy]pyridine

To a solution of 3-pyridinol (4.32 g, 45 mmol) in dimethylformamide (50 mL) was added sodium hydride (1.35 g of a 80% suspension in mineral oil, 45 mmol). The mixture was stirred for 1 h at room temperature and 3,5-dibromopyridine (5.92 g, 25 mmol) was added. The mixture was heated for 20 h at 130° C., then cooled to room temperature and poured into water (300 mL). The aqueous phase was extracted with diethyl ether (3×100 mL) and the organic phase was washed with water (2×100 mL) and brine (100 mL), then dried (MgSO4), filtered and concentrated by rotary evaporation. The crude product was purified by column chromatography, eluting with ethyl acetate/cyclohexane (30/70, v/v). Selected fractions containing the product were concentrated via rotary evaporation to give 3.5 g (56%) of a yellow oil.

1. temperatureThe mixture was heated for 20 h at 130° C.
2. temperaturecooled to room temperature
3. extractionThe aqueous phase was extracted with diethyl ether (3×100 mL)
4. washthe organic phase was washed with water (2×100 mL) and brine (100 mL)
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated by rotary evaporation
8. customThe crude product was purified by column chromatography
9. washeluting with ethyl acetate/cyclohexane (30/70
10. additionSelected fractions containing the product
11. concentrationwere concentrated via rotary evaporation

ORD record

ord-1c543c7083224fcda977201cdb6acd28

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07101896B2