反应 #2487477

反应方程式

ammonium chloride

5-chloromethylfuran-2-carbonitrile

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

sodium hydride

→

title compound

收率 14.4%

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

收率 14.4%

溶剂

water

N,N-dimethylformamide

N,N-dimethylformamide

反应条件

后处理

1. 1
   温度cooling
2. 2
   workup.STIRRINGat room temperature, and the mixture was stirred at 80° C. for 14 hours
3. 3
   萃取followed by extraction with ethyl acetate
4. 4
   洗涤The organic layer was washed with water and saturated brine successively
5. 5
   干燥dried over anhydrous magnesium sulfate
6. 6
   浓缩concentrated under reduced pressure
7. 7
   其他The residue was purified by aminopropylated silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

实验过程

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).

来源