反応 #70939

反応方程式

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

potassium carbonate

methylamine

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

→

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

溶媒

dimethylformamide

ethanol

acetic acid

反応条件

後処理

1. 1
   温度The reaction mixture was heated
2. 2
   温度at reflux for two hours whereupon the solvent
3. 3
   その他was removed by evaporation under vacuum
4. 4
   温度to cool to room temperature
5. 5
   workup.ADDITIONpoured onto ice-cold 1 N aqueous hydrochloric acid (100 mL)
6. 6
   ろ過The resulting precipitate was filtered off
7. 7
   洗浄washed with water
8. 8
   その他dried
9. 9
   その他The residue was chromatographed over silica gel
10. 10
    その他evaporated

実験手順

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-nitro-phenyl)-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%).

出典