반응 #534193

반응 방정식

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

N-methyl-2-tributylstannyl-1H-pyrrole

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title compound

1-Ethyl-3-[7-(1-methyl-1H-pyrrol-2-yl)-5-pyridin-3-yl-benzothiazol-2-yl]-urea

용매

DMF

반응 조건

후처리

1. 1
   기타The reaction mixture was degassed for half an hour
2. 2
   기타The reaction mixture was 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.ADDITIONadded water
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 by prep-HPLC

실험 절차

To a solution of 1-ethyl-3-(7-iodo-5-pyridin-3-yl-benzothiazol-2-yl)-urea (0.10 g, 0.24 mmol) in DMF (2.0 mL) was added N-methyl-2-tributylstannyl-1H-pyrrole (0.18 g, 0.47 mmol) under nitrogen atmosphere at room temperature. The reaction mixture was degassed for half an hour followed by the addition of tetrakis(triphenylphosphine)palladium(0) (0.027 g, 0.024 mmol). The reaction mixture was again degassed for half an hour and then heated at 120° C. for 20 h under nitrogen atmosphere. After the completion of the reaction (TLC monitoring), DMF was distilled off, added water 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 by prep-HPLC to provide the title compound as off white solid (0.005 g, 6.0%).

출처