반응 #43408

반응 방정식

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

용매

1,4-dioxane

반응 조건

후처리

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

실험 절차

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%).

출처