반응 #2487474

반응 방정식

sodium hydrogen carbonate

6-[2-(butan-2-yl)-6-chloro-5-methoxyindol-1-ylmethyl]pyridine-2-carboxamide

triethylamine

trifluoroacetic anhydride

→

title compound

수율 87.3%

6-[2-(Butan-2-yl)-6-chloro-5-methoxyindol-1-ylmethyl]pyridine-2-carbonitrile

수율 87.3%

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 6-[2-(butan-2-yl)-6-chloro-5-methoxyindol-1-ylmethyl]pyridine-2-carboxamide (118 mg) in dichloromethane (1.6 mL) were successively added triethylamine (0.225 mL) and trifluoroacetic anhydride (0.112 mL) under ice-cooling. This mixture was stirred at room temperature for 22 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 (98 mg). 1H-NMR (CDCl3) δ ppm: 0.86 (3H, t, J=7.4 Hz), 1.24 (3H, d, J=6.8 Hz), 1.45-1.80 (2H, m), 2.60-2.75 (1H, m), 3.93 (3H, s), 5.40 (2H, s), 6.31 (1H, s), 6.50-6.65 (1H, m), 7.11 (1H, s), 7.14 (1H, s), 7.50-7.70 (2H, m).

출처