Reaktion #43408

Reaktionsgleichung

1,1-dimethylethyl [2-chloro-5-fluoro-6-(methyloxy)-3-pyridinyl]carbamate

caesium fluoride

tributyl[1-(ethyloxy)ethenyl]stannane

potassium fluoride

→

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

Lösungsmittel

1,4-dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationthe mixture was filtered through Kieselguhr
2. 2
   Waschenwashing with 1,4-dioxane
3. 3
   workup.ADDITIONEthyl acetate and water were added to the filtrate
4. 4
   SonstigeThe phases were separated
5. 5
   Extraktionthe aqueous phase extracted twice with ethyl acetate
6. 6
   TrocknenThe combined organic extracts were dried over magnesium sulphate
7. 7
   Sonstigeevaporated
8. 8
   SonstigeThe residue was rapidly chromatographed
9. 9
   Wascheneluting with 25-50% dichloromethane in hexane affording the product as a light brown oil (22.2 g, 99%)

Vorschrift

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%).

Quelle