반응 #2487476

반응 방정식

sodium hydrogen carbonate

5-(6-chloro-5-methoxy-2-phenylindol-1-ylmethyl)furan-2-carboxamide

triethylamine

trifluoroacetic anhydride

→

title compound

수율 77.4%

5-(6-Chloro-5-methoxy-2-phenylindol-1-ylmethyl)furan-2-carbonitrile

수율 77.4%

용매

dichloromethane

반응 조건

후처리

1. 1
   온도cooling
2. 2
   추출followed by extraction with ethyl acetate
3. 3
   세척The organic layer was washed with saturated brine
4. 4
   건조dried over anhydrous sodium sulfate
5. 5
   농축concentrated under reduced pressure
6. 6
   기타The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

실험 절차

To a solution of 5-(6-chloro-5-methoxy-2-phenylindol-1-ylmethyl)furan-2-carboxamide (194 mg) in dichloromethane (2.5 mL) were successively added triethylamine (0.355 mL) and trifluoroacetic anhydride (0.177 mL) under ice-cooling. This mixture was stirred at room temperature for 8 hours. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (143 mg). 1H-NMR (CDCl3) δ ppm: 3.95 (3H, s), 5.23 (2H, s), 6.00-6.10 (1H, m), 6.50-6.60 (1H, m), 6.98 (1H, d, J=3.6 Hz), 7.16 (1H, s), 7.25-7.35 (1H, m), 7.40-7.55 (5H, m).

출처