反应 #2487476

反应方程式

sodium hydrogen carbonate

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

triethylamine

trifluoroacetic anhydride

→

title compound

收率 77.4%

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

收率 77.4%

溶剂

dichloromethane

反应条件

后处理

1. 1
   温度cooling
2. 2
   萃取followed by extraction with ethyl acetate
3. 3
   洗涤The organic layer was washed with saturated brine
4. 4
   干燥dried over anhydrous sodium sulfate
5. 5
   浓缩concentrated under reduced pressure
6. 6
   其他The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

实验过程

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).

来源