Triphenylphosphine → HCID 15895874, compound

3-(3,5-Dimethoxypyridin-4-yl)-1-propanol (0.60 g, 3.0 mmol) obtained in Example 1 and triphenylphosphine (1.18 g, 4.5 mmol) are dissolved in THF (30 ml), and thereto are successively added with stirring diisopropyl azodicarboxylate (0.78 g, 3.9 mmol) and 2-(3-bromophenoxy)-3-pyridinol (1.04 g, 3.9 mmol) obtained in Reference Example 11 under ice-cooling. The mixture is stirred at room temperature for 30 minutes, and the reaction solution is concentrated under reduced pressure. To the residue is added ethyl acetate (50 ml), and the mixture is extracted with a 10% aqueous hydrochloric acid solution (50 ml×2). The pH value of the aqueous layer is adjusted to pH 12 with potassium carbonate, and the mixture is extracted with ethyl acetate (100 ml×2). The organic layer is washed with a saturated brine (50 ml×2), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: chloroform/methanol) to give 2-(3-bromophenoxy)-3-[3-(3,5-dimethoxypyridin-4-yl)propoxyl]pyridine, which is further treated with fumaric acid to give the title compound (1.26 g), m.p. 106-154° C.

1. customobtained in Reference Example 11 under ice-
2. temperaturecooling
3. concentrationthe reaction solution is concentrated under reduced pressure
4. additionTo the residue is added ethyl acetate (50 ml)
5. extractionthe mixture is extracted with a 10% aqueous hydrochloric acid solution (50 ml×2)
6. extractionthe mixture is extracted with ethyl acetate (100 ml×2)
7. washThe organic layer is washed with a saturated brine (50 ml×2)
8. dry with materialdried over anhydrous magnesium sulfate
9. concentrationconcentrated under reduced pressure
10. customThe residue is purified by silica gel column chromatography (eluent: chloroform/methanol)

ORD record

ord-54ac8755b6f9468bbe5e95b62631cae2

Source dataset

uspto-grants-2003_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06555557B1