반응 #90284

반응 방정식

ethyl 3-oxo-3-(2-(trifluoromethyl)pyridin-3-yl)propanoate

potassium carbonate

methylamine

1-(3,4-bis-benzyloxy-5-nitrophenyl)-2-bromo-ethanone

→

ethyl 5-(3,4-bis(benzyloxy)-5-nitrophenyl)-1-methyl-2-(2-(trifluoromethyl)pyridin-3-yl)-1H-pyrrole-3-carboxylate

용매

dimethylformamide

ethanol

acetic acid

반응 조건

후처리

1. 1
   온도The reaction mixture was heated
2. 2
   온도at reflux for two hours whereupon the solvent
3. 3
   기타was removed by evaporation under vacuum
4. 4
   온도to cool to room temperature
5. 5
   workup.ADDITIONpoured onto ice-cold 1 N aqueous hydrochloric acid (100 mL)
6. 6
   여과The resulting precipitate was filtered off
7. 7
   세척washed with water
8. 8
   기타dried
9. 9
   기타The residue was chromatographed over silica gel
10. 10
    기타evaporated

실험 절차

To a stirred solution of methylamine (0.63 mL, 33% EtOH solution, 5 mmol) in a mixture of ethanol (25 mL) and acetic acid (0.5 mL) at room temperature was added ethyl 3-oxo-3-(2-(trifluoromethyl)pyridin-3-yl)propanoate (1.305 g, 5 mmol). The reaction mixture was heated at reflux for two hours whereupon the solvent was removed by evaporation under vacuum. To a solution of the crude product in dimethylformamide (25 mL) was added potassium carbonate (2.07 g, 15 mmol) in one portion followed by 1-(3,4-bis-benzyloxy-5-nitrophenyl)-2-bromo-ethanone (2.51 g, 5.50 mmol) and the mixture was then stirred at 100° C. Once no starting material was detectable, the reaction mixture was allowed to cool to room temperature and poured onto ice-cold 1 N aqueous hydrochloric acid (100 mL). The resulting precipitate was filtered off, washed with water and dried. The residue was chromatographed over silica gel. Homogeneous fractions were pooled and evaporated to give ethyl 5-(3,4-bis(benzyloxy)-5-nitrophenyl)-1-methyl-2-(2-(trifluoromethyl)pyridin-3-yl)-1H-pyrrole-3-carboxylate, 2.492 g (79%).

출처