Réaction #2487455

Équation de réaction

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

sodium hydride

ammonium chloride

methyl 6-chloromethylpyridine-2-carboxylate

→

title compound

Rendement 9.4%

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

Rendement 9.4%

Solvants

N,N-dimethylformamide

ethyl acetate

Conditions de réaction

Traitement

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

Mode opératoire

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).

Source