反应 #2487460

反应方程式

Water

6-chloromethylpyridine-2-carbonitrile

5-methoxy-2-phenyl-1H-indole

sodium hydride

→

title compound

收率 75.0%

6-(5-Methoxy-2-phenylindol-1-ylmethyl)pyridine-2-carbonitrile

收率 75.0%

溶剂

N,N-dimethylformamide

反应条件

后处理

1. 1
   温度cooling
2. 2
   workup.STIRRINGby stirring at 80° C. overnight
3. 3
   萃取followed by extraction with ethyl acetate
4. 4
   洗涤The organic layer was washed with water and saturated brine
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 silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

实验过程

To a solution of 5-methoxy-2-phenyl-1H-indole (200 mg) in N,N-dimethylformamide (5 mL) was added sodium hydride (dispersed in liquid paraffin, 50% or more, 45 mg) under ice-cooling. This mixture was stirred for 30 minutes at room temperature. Subsequently, 6-chloromethylpyridine-2-carbonitrile (216 mg) was added thereto, followed by stirring at 80° C. overnight. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium 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 (228 mg). 1H-NMR (DMSO-d6) δ ppm: 3.77 (3H, s), 5.55 (2H, s), 6.55-6.65 (1H, m), 6.77 (1H, dd, J=2.4, 8.8 Hz), 6.91 (1H, dd, J=1.5, 7.4 Hz), 7.13 (1H, d, J=2.4 Hz), 7.26 (1H, d, J=8.8 Hz), 7.35-7.55 (5H, m), 7.85-7.95 (2H, m).

来源