Réaction #2487476

Équation de réaction

sodium hydrogen carbonate

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

triethylamine

trifluoroacetic anhydride

→

title compound

Rendement 77.4%

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

Rendement 77.4%

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   Températurecooling
2. 2
   Extractionfollowed by extraction with ethyl acetate
3. 3
   LavageThe organic layer was washed with saturated brine
4. 4
   Séchagedried over anhydrous sodium sulfate
5. 5
   Concentrationconcentrated under reduced pressure
6. 6
   AutreThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Mode opératoire

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).

Source