Reacción #2487455

Ecuación de reacción

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

sodium hydride

ammonium chloride

methyl 6-chloromethylpyridine-2-carboxylate

→

title compound

Rendimiento 9.4%

Methyl 6-(5-methoxy-2-phenylindol-1-ylmethyl)pyridine-2-carboxylate

Rendimiento 9.4%

Disolventes

N,N-dimethylformamide

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooling
2. 2
   Temperaturacooling
3. 3
   workup.STIRRINGstirred for 30 minutes at room temperature
4. 4
   workup.STIRRINGby stirring at 80° C. for 18 hours
5. 5
   Otroto separate the organic layer
6. 6
   ExtracciónThe aqueous layer was extracted twice with ethyl acetate
7. 7
   LavadoThe combined organic layer was washed with saturated brine
8. 8
   Secadodried over anhydrous sodium sulfate
9. 9
   Concentraciónconcentrated under reduced pressure
10. 10
    OtroThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Procedimiento

Under an argon atmosphere, to a solution of 5-methoxy-2-phenyl-1H-indole (582 mg) in N,N-dimethylformamide (13 mL) was added sodium hydride (dispersed in liquid paraffin, 55% or more, 171 mg) under ice-cooling. This mixture was stirred for 5 minutes under ice-cooling, and then stirred for 30 minutes at room temperature. Subsequently, methyl 6-chloromethylpyridine-2-carboxylate (483 mg) was added thereto, followed by stirring at 80° C. for 18 hours. The reaction mixture was poured into an ice-cooled saturated aqueous ammonium chloride solution, and then ethyl acetate was added to the mixture to separate the organic layer. The aqueous layer was extracted twice with ethyl acetate. The combined organic layer was washed with saturated brine, dried over anhydrous sodium 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 (91 mg). 1H-NMR (CDCl3) δ ppm: 3.87 (3H, s), 4.02 (3H, s), 5.58 (2H, s), 6.60-6.75 (2H, m), 6.81 (1H, dd, J=2.5, 8.8 Hz), 7.02 (1H, d, J=8.8 Hz), 7.15 (1H, d, J=2.5 Hz), 7.30-7.45 (5H, m), 7.60-7.70 (1H, m), 7.95-8.05 (1H, m).

Fuente