반응 #2487477

반응 방정식

ammonium chloride

5-chloromethylfuran-2-carbonitrile

5-methoxy-2-(1-methylcyclopropyl)-1H-indole

sodium hydride

→

title compound

수율 14.4%

5-[5-Methoxy-2-(1-methylcyclopropyl)indol-1-ylmethyl]furan-2-carbonitrile

수율 14.4%

용매

water

N,N-dimethylformamide

N,N-dimethylformamide

반응 조건

후처리

1. 1
   온도cooling
2. 2
   workup.STIRRINGat room temperature, and the mixture was stirred at 80° C. for 14 hours
3. 3
   추출followed by extraction with ethyl acetate
4. 4
   세척The organic layer was washed with water and saturated brine successively
5. 5
   건조dried over anhydrous magnesium sulfate
6. 6
   농축concentrated under reduced pressure
7. 7
   기타The residue was purified by aminopropylated silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

실험 절차

To a solution of 5-methoxy-2-(1-methylcyclopropyl)-1H-indole (155 mg) in N,N-dimethylformamide (3 mL) was added sodium hydride (dispersed in liquid paraffin, 50% or more, 39 mg) under ice-cooling. This mixture was stirred at room temperature for 50 minutes. Subsequently, a solution of 5-chloromethylfuran-2-carbonitrile (131 mg) in N,N-dimethylformamide (0.5 mL) was added thereto at room temperature, and the mixture was stirred at 80° C. for 14 hours. To the reaction mixture were added saturated aqueous ammonium chloride solution and water, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine successively, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by aminopropylated silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (34 mg). 1H-NMR (CDCl3) δ ppm: 0.70-1.00 (4H, m), 1.35 (3H, s), 3.83 (3H, s), 5.45 (2H, s), 5.95-6.00 (1H, m), 6.20-6.30 (1H, m), 6.75-6.85 (1H, m), 6.90-7.10 (3H, m).

출처