تفاعل #507849

معادلة التفاعل

N-[3-bromo-6-(methyloxy)-2-pyridinyl]-2,2-dimethylpropanamide

n-butyl acrylate

dicyclohexylmethylamine

→

product

المردود 95.4%

Butyl (2E)-3-[2-[(2,2-dimethylpropanoyl)amino]-6-(methyloxy)-3-pyridinyl]-2-propenoate

المردود 95.4%

المذيبات

DCM

ظروف التفاعل

المعالجة

1. 1
   أخرىin dry
2. 2
   أخرىdegassed 1,4-dioxane (600 ml)
3. 3
   أخرىThe reaction was then evaporated
4. 4
   workup.ADDITIONwater (1000 ml) was added
5. 5
   استخلاصthe mixture was extracted with Et2O (3×500 ml)
6. 6
   تجفيفThe combined organic solvents were then dried (MgSO4)
7. 7
   ترشيحfiltered
8. 8
   أخرىevaporated
9. 9
   أخرىto give the crude product
10. 10
    أخرىchromatographed (10-30% EtOAc:40-60 petroleum ether)
11. 11
    أخرىdried in vacuo

الإجراء التجريبي

A mixture of N-[3-bromo-6-(methyloxy)-2-pyridinyl]-2,2-dimethylpropanamide (78.738 g, 274 mmol), bis(tri-t-butylphosphine)palladium(0) (1 g, 1.957 mmol) and tris(dibenzylideneacetone)dipalladium(0) (0.892 g, 0.974 mmol) in dry, degassed 1,4-dioxane (600 ml) was treated with n-butyl acrylate (47.1 ml, 329 mmol) and dicyclohexylmethylamine (64.5 ml, 302 mmol). The reaction mixture was then heated at 80° C. for 4 h and then at 120° C. for 3 h. The reaction was then evaporated and water (1000 ml) was added and the mixture was extracted with Et2O (3×500 ml). The combined organic solvents were then dried (MgSO4), filtered, evaporated to give the crude product. This was then dissolved in DCM (300 ml) and chromatographed (10-30% EtOAc:40-60 petroleum ether) and then dried in vacuo to give product as a white solid (87.412 g, 95%).

المصدر