反应 #2487455

反应方程式

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

sodium hydride

ammonium chloride

methyl 6-chloromethylpyridine-2-carboxylate

→

title compound

收率 9.4%

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

收率 9.4%

溶剂

N,N-dimethylformamide

ethyl acetate

反应条件

后处理

1. 1
   温度cooling
2. 2
   温度cooling
3. 3
   workup.STIRRINGstirred for 30 minutes at room temperature
4. 4
   workup.STIRRINGby stirring at 80° C. for 18 hours
5. 5
   其他to separate the organic layer
6. 6
   萃取The aqueous layer was extracted twice with ethyl acetate
7. 7
   洗涤The combined organic layer was washed with saturated brine
8. 8
   干燥dried over anhydrous sodium sulfate
9. 9
   浓缩concentrated under reduced pressure
10. 10
    其他The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

实验过程

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).

来源