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Method for preparing methyl 2-phenyl-3-(2'-pyridyl)-3H-indole formate compound through aluminum catalysis

A technology for the catalytic preparation of methyl indole carboxylate, which is applied in the field of chemical intermediate preparation, and can solve the problems of many reaction steps, low reaction efficiency, and limited application range of the reaction.

Inactive Publication Date: 2020-09-22
JIYANG COLLEGE OF ZHEJIANG A & F UNIV
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

The reported preparation methods of 3H-indole compounds are mainly obtained through multi-step coupling and condensation through transition metal catalysis, but there are many problems such as many reaction steps, low reaction efficiency and not wide range of reaction applications.

Method used

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  • Method for preparing methyl 2-phenyl-3-(2'-pyridyl)-3H-indole formate compound through aluminum catalysis
  • Method for preparing methyl 2-phenyl-3-(2'-pyridyl)-3H-indole formate compound through aluminum catalysis
  • Method for preparing methyl 2-phenyl-3-(2'-pyridyl)-3H-indole formate compound through aluminum catalysis

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Embodiment 1: the preparation of 4a product

[0039] At room temperature, add 3mmol of 2-iodobenzoylformyl methyl ester, 6mmol of benzylamine and 3mmol of 2-pyridinecarbaldehyde into a 25mL round-bottom flask respectively, then add 10mL of DMF-DMSO mixed solution, 0.3 mmol of triethylaluminum and 6 mmol of sodium carbonate, the reaction was stirred at 70°C for 5 hours. After cooling, add 20mL saturated aqueous sodium chloride solution to the system, extract 3 times with ethyl acetate, 20mL each time, combine the organic phases, dry with anhydrous sodium sulfate, evaporate the solvent, and obtain by 200-300 mesh silica gel column chromatography Product 4a (90% yield, white solid). 4a 1 H-NMR spectrum see figure 1 , 4a 13 C-NMR spectrum see figure 2 .

[0040]

[0041] 2-Phenyl-3-(pyridin-2-yl)-3H-indole-3-carboxylate mp: 125.7-134.6℃; 1HNMR (400MHz, Chloroform-d) δ8.56(d, J=4.8Hz, 1H), 8.09(d, J=7.6Hz, 2H), 7.75(d, J=7.8Hz, 1H), 7.51(t, J=8.2Hz, 2H), 7.44(t, ...

Embodiment 2

[0044] Embodiment 2: Preparation of 4b product

[0045] At room temperature, add 3mmol of 3-methyl-2-iodobenzoylformic acid methyl ester, 6mmol of benzylamine and 3mmol of 2-pyridinecarbaldehyde in a 25mL round bottom flask respectively, and then add 10mL of DMF- DMSO mixed solution, 0.3mmol of triethylaluminum and 6mmol of sodium carbonate were stirred at 70°C for 5 hours. After cooling, add 20 mL of saturated aqueous sodium chloride solution to the system, extract 3 times with ethyl acetate, 20 mL each time, combine the organic phases, dry with anhydrous sodium sulfate, evaporate the solvent, and obtain Product 4b (89% yield, white solid). 4b 1 H-NMR spectrum see image 3 , 4b 13 C-NMR spectrum see Figure 4 .

[0046]

[0047] 5-Methyl-2-phenyl-3-(pyridin-2-yl)-3H-indole-3-carboxylate mp: 172.7-175.7℃;

[0048] 1 H NMR (400MHz, Chloroform-d) δ8.50(dt, J=4.7,1.5Hz,1H),8.00(dt, J=6.9,1.6Hz,2H),7.56(d,J=7.8Hz,1H) ,7.44(td,J=7.8,1.9Hz,1H), 7.33–7.23(m,4H),7.21–7.15(...

Embodiment 3

[0051] Embodiment 3: Preparation of 4c product

[0052] At room temperature, add 3mmol of 3-methoxy-2-iodobenzoylformic acid methyl ester, 6mmol of benzylamine and 3mmol of 2-pyridinecarbaldehyde in a 25mL round bottom flask respectively, and then add 10mL of DMF in sequence - DMSO mixed solution, 0.3 mmol of triethylaluminum and 6 mmol of sodium carbonate, and the reaction was stirred at 70° C. for 5 hours. After cooling, add 20 mL of saturated aqueous sodium chloride solution to the system, extract 3 times with ethyl acetate, 20 mL each time, combine the organic phases, dry with anhydrous sodium sulfate, evaporate the solvent, and obtain Product 4c (86% yield, white solid). 4c 1 H-NMR spectrum see Figure 5 , 4c 13 C-NMR spectrum see Figure 6 .

[0053]

[0054] 5-Methoxy-2-phenyl-3-(pyridin-2-yl)-3H-indole-3-carboxylate mp: 162.7-165.4℃;

[0055] 1 H NMR (400MHz, Chloroform-d) δ8.59(dt, J=4.5, 1.5Hz, 1H), 8.09–8.01(m, 2H), 7.64(d, J=8.5Hz, 1H), 7.49(td, J=7.8,1...

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Abstract

The invention discloses a method for preparing a methyl 2-phenyl-3-(2'-pyridyl)-3H-indole formate compound through aluminum catalysis. The method comprises reacting a methyl 2-iodobenzoyl formate compound as shown in a formula (I), benzylamine as shown in a formula (II) and a 2-pyridylaldehyde compound as shown in a formula (III) in a mixed solvent of N,N-dimethylformamide (DMF) and dimethyl sulfoxide (DMSO) by adopting triethyl aluminum as a catalyst and sodium carbonate as an alkali, and carrying out aftertreatment on a reactant to obtain the methyl 2-phenyl-3-(2'-pyridyl)-3H-indole formatecompound. The method is excellent in yield, relatively low in equipment requirement, wide in catalytic system adaptability and suitable for large-scale production of material chemical intermediates. The chemical equation is shown in the specification.

Description

technical field [0001] The invention belongs to the technical field of chemical intermediate preparation, and in particular relates to a method for preparing 2-phenyl-3-(2'-pyridyl)-3H-indolecarboxylic acid methyl ester compounds by aluminum catalysis. Background technique [0002] 3H-indole compounds have high sensitivity to the environment, and a large number of probes are widely used to study microenvironment and supramolecular systems. 3H-indole molecule has good surface activity and positive charge, and its interaction with molecular order shows many unique properties. 3H-indole is widely used in biomedical fields such as biomacromolecule labeling, photodynamic therapy, DNA sequencing, and pH probes. In addition, 3H-indocyanine dyes with 3H-indole as the backbone have the characteristics of high stability, large molar extinction coefficient, wide tunable range of absorption wavelength and strong structure modification, etc., and have been used in optical disk storage m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04
CPCC07D401/04
Inventor 徐润生傅旭晴李静宁徐慧雅
Owner JIYANG COLLEGE OF ZHEJIANG A & F UNIV
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