2,3-disubstituted indole derivative and preparation method thereof

An indole and disubstituted technology, applied in the field of 2,3-disubstituted indole derivatives and their preparation, can solve the problems of expensive raw material sources, low reaction yield, long reaction steps, etc., and achieve wide application The effect of prospect, simple preparation method and high compatibility

Inactive Publication Date: 2018-06-22
YANCHENG INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The existing methods for preparing indole ring derivatives are often accompanied by the following disadvantages: the source of raw materials is relatively expensive, two or more catalysts are required for joint catalysis, the reaction needs to add various ligands or additives, the reaction time is too long, and the reaction substrate is not easy Preparation, the reaction steps are too long, too many by-products are difficult to separate and purify, the reaction yield is not high, the structure of the product is not easy to expand, the degree of atom economy is not high, and even the use of dangerous azide raw materials, etc.

Method used

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  • 2,3-disubstituted indole derivative and preparation method thereof
  • 2,3-disubstituted indole derivative and preparation method thereof
  • 2,3-disubstituted indole derivative and preparation method thereof

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preparation example Construction

[0027] The present invention proposes a method for preparing 2,3-disubstituted indole derivatives, which includes: constructing 2,3-disubstituted indole derivatives through palladium-catalyzed cascade reactions with alkynyl anilines and substituted bromobenzenes of different structures compound.

[0028] Further, in a preferred embodiment of the present invention, a method for preparing a 2,3-disubstituted indole derivative provided by the present invention comprises the following steps:

[0029] a. Precursor compound synthesis;

[0030] b. Synthesis of the target product;

[0031] c. Purification.

[0032] Wherein, step a, b synthetic route is as follows:

[0033]

[0034] Step a comprises the following steps: in an anhydrous and oxygen-free system, adding o-alkynyl aniline and trifluoroacetic acid into a carbon tetrachloride solvent, adding triphenylphosphine as a catalyst, and adding a certain amount of triethylamine, ice Stir in a water bath environment for 10 minut...

Embodiment 1

[0046] A preparation method of 2,3-disubstituted indole derivatives comprises the following steps:

[0047] a. Precursor compound synthesis:

[0048] In an anhydrous and oxygen-free system, add 20mmol o-tolylethynylaniline, 20mmol trifluoroacetic acid and 40ml carbon tetrachloride solvent into a 100ml reaction flask, then add 50mmol triphenylphosphine and 22mmol triethylamine, and place in an ice-water bath Stir in the environment for 10 minutes, then heat and reflux for 3 hours, stop the reaction, add water to wash several times, then extract and concentrate with ethyl acetate, dry with anhydrous magnesium sulfate, and finally use acetic acid with a volume ratio of 1: (40-80) The mixture of ethyl acetate and petroleum ether was used as the eluent for column chromatography separation and purification. The volume ratio of ethyl acetate and petroleum ether in the mixture was 1:60, and about 16.3 mmol of the precursor compound was obtained.

[0049] b. Target product synthesis:

...

Embodiment 2

[0054] A preparation method of 2,3-disubstituted indole derivatives comprises the following steps:

[0055] a. Precursor compound synthesis:

[0056] In an anhydrous and oxygen-free system, add 20mmol of o-hexynylaniline, 17mmol of trifluoroacetic acid and 40ml of carbon tetrachloride solvent into a 100ml reaction flask, then add 50mmol of triphenylphosphine and 22mmol of triethylamine in an ice-water bath environment Stir for 10 minutes, then heat and reflux for 3 hours, stop the reaction, add water to wash several times, then extract and concentrate with ethyl acetate, dry with anhydrous magnesium sulfate, and finally use ethyl acetate with a volume ratio of 1: (40-80) The mixture of ester and petroleum ether was used as the eluent for column chromatography separation and purification. The volume ratio of ethyl acetate to petroleum ether in the mixture was 1:60, and about 16.5 mmol of the precursor compound was obtained.

[0057] b. Target product synthesis:

[0058] Put 1...

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Abstract

Provided is a 2,3-disubstituted indole derivative. The 2,3-disubstituted indole derivative has great biological activity and can be widely applied to light chemical industry, agriculture, medicine andother fields. Additionally, the invention also relates to a preparation method of the 2,3-disubstituted indole derivative. According to the preparation method, alkynyl aniline and substituted bromobenzene which are of different structures are subjected to a cascade reaction catalyzed by palladium to form a 2,3-disubstituted indole compound. Therefore, the method is simple, convenient, efficient and environmentally friendly.

Description

technical field [0001] The invention relates to the field of indole derivatives, and in particular to a 2,3-disubstituted indole derivative and a preparation method thereof. Background technique [0002] Indole ring is an aromatic heterocyclic organic compound, one of the most widely distributed heterocyclic compounds in nature, and is widely used in light chemical, pesticide, medicine and other fields. Indole has a flower-like scent and is a constituent of many floral scents, such as orange blossom, and is also used to make perfumes. Indole and its derivatives not only have a wide range of biological activities, but also have extended applications in the field of anti-tumor, such as the anti-inflammatory drug indomethacin and the vasodilator drug Propola. The functionally modified indole ring structure can produce a series of biological and pharmaceutically active compounds, which makes indole ring derivatives play an increasingly important role in the development of drugs...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/18C07D209/12
CPCC07D209/12C07D209/18
Inventor 李立冬吴玉芹马岗岥刘伟许琦
Owner YANCHENG INST OF TECH
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