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Synthesis method of indole derivative

A technology of indole derivatives and synthetic methods, applied in the direction of organic chemistry, can solve problems such as application limitations, and achieve the effects of simple operation, high product yield, and mild reaction conditions

Inactive Publication Date: 2016-06-22
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in the above method, pyrrole derivatives need to be pre-functionalized and the raw materials for the reaction are difficult to prepare, which limits their application in the synthesis of indole derivatives.

Method used

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  • Synthesis method of indole derivative
  • Synthesis method of indole derivative
  • Synthesis method of indole derivative

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028]

[0029] In a 10mL Schlenk reaction flask, add palladium acetate Pd(OAc) successively under air 2 (4.5mg, 0.02mmol), N-methyl-2-phenylpyrrole 2a (0.2mmol), chloropropiophenone 3a (133mg, 0.8mmol), copper acetate Cu(OAc) 2 (145mg, 0.8mmol) sodium acetate NaOAc (65mg, 0.8mmol), PivOH pivalate (20mg, 0.2mmol), tetrabutylammonium bromide TBAB (32mg, 0.1mmol) and 2.5mL N,N-dimethylformaldehyde A mixed solvent of amide and dimethyl sulfoxide was stirred at 130°C for 24 hours. After cooling to room temperature, filter through diatomaceous earth, add 20 mL of water to the filtrate, extract the aqueous phase (2×15 mL) with dichloromethane, and separate the organic phase. The organic phases were mixed, dried over anhydrous magnesium sulfate, and filtered. The volatile components were removed under reduced pressure, and then separated by silica gel column chromatography (eluent: petroleum ether (60-90°C) / ethyl acetate / dichloromethane, v / v / v=250:8:20), The product 1a (53 mg, ...

Embodiment 2

[0031] Reaction steps and operation are with embodiment 1, and difference with embodiment 1 is that catalyst is palladium chloride PdCl 2 . The reaction was stopped, and the target product 1a (39 mg, yield 47%) was obtained after post-treatment. It shows that palladium chloride can also be used as a catalyst for the reaction, but it is not the best catalyst.

Embodiment 3

[0033] Reaction steps and operation are with embodiment 1, and difference with embodiment 1 is that catalyst is tetrakis triphenyl phosphopalladium Pd (PPh 3 ) 4 . The reaction was stopped, and the target product 1a (25 mg, yield 30%) was obtained after post-processing. It shows that tetrakistriphenylphosphopalladium can also be used as a catalyst for the reaction, but it is not the best catalyst.

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Abstract

The invention discloses a synthesis method of an indole derivative with wide bioactivity. The method includes: taking a simple pyrrole derivative and a beta-chloroketone derivative as the raw materials, using a palladium salt as the catalyst, adding an oxidant and an additive, and under an alkaline condition, carrying out Domino pyrrole alkenylation-Diels-Alder cycloaddition-dehydro-aromatization reaction to synthesize the indole derivative. Compared with the reported indole derivative synthesis method, the method provided by the invention has the advantages of easily available raw materials, simple operation, wide application range, and mild synthesis reaction conditions.

Description

technical field [0001] The invention discloses a synthesis method of indole derivatives with wide biological activities. Using simple pyrrole derivatives and β-chloroketone derivatives as raw materials, palladium salts as catalysts, adding oxidants and additives, heating and reacting under alkaline conditions, and undergoing Domino pyrrole enylation-Diels-Alder cycloaddition- Synthesis of Indole Derivatives by Dehydroaromatization. Compared with the reported synthetic methods of indole derivatives, the present invention has easy-to-obtain raw materials, simple operation, wide application range and mild synthetic reaction conditions. Background technique [0002] Indole and its derivatives are important fine chemical raw materials and chemical products, and are widely used in the fields of industry, agriculture and medicine. Indole compounds, as an important class of heterocyclic compounds, have a wide range of biological activities. In 2009, Hofmann-La Roche Co., Ltd. pat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/08C07D209/10C07D409/04C07D405/14
Inventor 余正坤郭腾龙
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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