反应详情

Trifluoroacetic anhydride (12.0 g, 57.1 mmol) was added dropwise to a mixture of 1-(cyclohexyl)methyl-7-methoxy-1H-indole-3-carboxylic acid amide (4.1 g, 14.3 mmol), triethylamine (11.6 g, 115 mmol), and 1,4-dioxane (250 ml) under ice-water cooling. The resulting mixture was stirred at room temperature for 12 h. Water (30 ml) was added and the resulting mixture was concentrated in vacuo. Water (300 ml) was added to the obtained residue, and the mixture was extracted with dichloromethane (4×300 ml). The organic layers were combined, washed with 5% aqueous sodium hydrogen carbonate and brine, dried over magnesium sulfate, and concentrated in vacuo. The obtained residue was purified by column chromatography eluting with 10% (v/v) ethyl acetate in n-heptane to afford 1-(cyclohexyl)methyl-7-methoxy-1H-indole-3-carbonitrile as a crystalline solid (2.48 g).

1. concentrationthe resulting mixture was concentrated in vacuo
2. additionWater (300 ml) was added to the obtained residue
3. extractionthe mixture was extracted with dichloromethane (4×300 ml)
4. washwashed with 5% aqueous sodium hydrogen carbonate and brine
5. dry with materialdried over magnesium sulfate
6. concentrationconcentrated in vacuo
7. customThe obtained residue was purified by column chromatography
8. washeluting with 10% (v/v) ethyl acetate in n-heptane