반응 #2487455

반응 방정식

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

sodium hydride

ammonium chloride

methyl 6-chloromethylpyridine-2-carboxylate

→

title compound

수율 9.4%

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

수율 9.4%

용매

N,N-dimethylformamide

ethyl acetate

반응 조건

후처리

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

실험 절차

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).

출처