Cesium fluoride → 1,1-Dimethylethyl [2-[1-(ethyloxy)ethenyl]-5-fluoro-6-(methyloxy)-3-pyridinyl]carbamate

Temperature

100 °C

A degassed solution of 1,1-dimethylethyl [2-chloro-5-fluoro-6-(methyloxy)-3-pyridinyl]carbamate (20 g, 72.2 mmol) in 1,4-dioxane (200 ml) was treated with bis(tri-tert-butylphosphine) palladium(0) (1.05 g), caesium fluoride (21.93 g) and tributyl[1-(ethyloxy)ethenyl]stannane (26.9 ml) then heated to 100° C. overnight. The cooled mixture was treated with 10% aqueous potassium fluoride solution. After 0.5 hour stirring, the mixture was filtered through Kieselguhr, washing with 1,4-dioxane. Ethyl acetate and water were added to the filtrate. The phases were separated and the aqueous phase extracted twice with ethyl acetate. The combined organic extracts were dried over magnesium sulphate and evaporated. The residue was rapidly chromatographed eluting with 25-50% dichloromethane in hexane affording the product as a light brown oil (22.2 g, 99%).

1. filtrationthe mixture was filtered through Kieselguhr
2. washwashing with 1,4-dioxane
3. additionEthyl acetate and water were added to the filtrate
4. customThe phases were separated
5. extractionthe aqueous phase extracted twice with ethyl acetate
6. dry with materialThe combined organic extracts were dried over magnesium sulphate
7. customevaporated
8. customThe residue was rapidly chromatographed
9. washeluting with 25-50% dichloromethane in hexane affording the product as a light brown oil (22.2 g, 99%)

ORD record

ord-7f2d49d4ac4a426ea06dc7242d782435

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07732460B2