Reaction #2487460

Reaction equation

Water

6-chloromethylpyridine-2-carbonitrile

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

sodium hydride

→

title compound

Yield 75.0%

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

Yield 75.0%

Solvents

N,N-dimethylformamide

Conditions

Workup

1. 1
   Temperaturecooling
2. 2
   workup.STIRRINGby stirring at 80° C. overnight
3. 3
   Extractionfollowed by extraction with ethyl acetate
4. 4
   WashThe organic layer was washed with water and saturated brine
5. 5
   Dryingdried over anhydrous magnesium sulfate
6. 6
   Concentrationconcentrated under reduced pressure
7. 7
   OtherThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Procedure

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).

Source