반응 #534218

반응 방정식

1-(7-bromo-5-pyridin-3-yl-benzothiazol-2-yl)-3-ethyl-urea

tributylallyltin

→

title compound

1-(7-Allyl-5-pyridin-3-yl-benzothiazol-2-yl)-3-ethyl-urea

용매

DMF

반응 조건

후처리

1. 1
   기타The reaction mixture was then degassed for half an hour
2. 2
   기타The reaction mixture was then again degassed for half an hour
3. 3
   기타After the completion of the reaction (TLC monitoring), DMF
4. 4
   workup.DISTILLATIONwas distilled off
5. 5
   workup.ADDITIONwater was added to the reaction mixture
6. 6
   추출extracted with ethyl acetate (×3)
7. 7
   건조The combined organic layer was dried over anhydrous Na2SO4
8. 8
   기타evaporated to dryness under reduced pressure
9. 9
   기타The crude residue was purified over silica gel (230-400 M)

실험 절차

To a solution of 1-(7-bromo-5-pyridin-3-yl-benzothiazol-2-yl)-3-ethyl-urea (0.14 g, 0.37 mmol) in DMF (2 mL) was added tributylallyltin (0.15 g, 0.45 mmol) under nitrogen atmosphere at room temperature. The reaction mixture was then degassed for half an hour followed by the addition of tetrakis(triphenylphosphine)palladium(0) (0.043 g, 0.0371 mmol). The reaction mixture was then again degassed for half an hour and heated at 120° C. for 20 h under nitrogen atmosphere. After the completion of the reaction (TLC monitoring), DMF was distilled off; water was added to the reaction mixture and extracted with ethyl acetate (×3). The combined organic layer was dried over anhydrous Na2SO4, and evaporated to dryness under reduced pressure. The crude residue was purified over silica gel (230-400 M) using EtOAc-MeOH (95:5) to provide the title compound as off white solid (0.034 g, 27%).

출처