Reaktion #7514

Reaktionsgleichung

water

ethyl 4-chloro-2-(2,3-dihydro-1H-indol-1-yl)-5-pyrimidinecarboxylate

potassium carbonate

4-(trifluoromethoxy)benzyl alcohol

→

title compound

Ausbeute 53.2%

ethyl 2-(2,3-dihydro-1H-indol-1-yl)-4-{[4-(trifluoromethoxy)benzyl]oxy}-5-pyrimidinecarboxylate

Ausbeute 53.2%

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto cool to room temperature
2. 2
   Extraktionwhich was followed by extraction with ethyl acetate
3. 3
   WaschenThe organic layer was washed with saturated brine
4. 4
   Trocknendried over anhydrous sodium sulfate
5. 5
   EinengenThe solvent was concentrated under reduced pressure
6. 6
   Wascheneluted with hexane-ethyl acetate (4:1)

Vorschrift

To a solution of ethyl 4-chloro-2-(2,3-dihydro-1H-indol-1-yl)-5-pyrimidinecarboxylate (520 mg, 1.72 mmol) in N,N-dimethylformamide (5 mL) was added potassium carbonate (829 mg, 6 mmol) and 4-(trifluoromethoxy)benzyl alcohol (384 mg, 2 mmol) and the mixture was stirred at 100° C. for 18 h. The reaction mixture was allowed to cool to room temperature and water was added, which was followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure and the residue was applied to silica gel column chromatography and eluted with hexane-ethyl acetate (4:1) to give the title compound (420 mg, 53%).

Quelle