Réaction #2487477

Équation de réaction

ammonium chloride

5-chloromethylfuran-2-carbonitrile

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

sodium hydride

→

title compound

Rendement 14.4%

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

Rendement 14.4%

Solvants

water

N,N-dimethylformamide

N,N-dimethylformamide

Conditions de réaction

Traitement

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

Mode opératoire

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).

Source