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Method for synthesizing diphenyl substituted indole compound

A synthetic method and compound technology, applied in the direction of organic chemistry, etc., can solve the problems that affect the wide application of the synthesis of pharmaceutical intermediates and low reaction yield, and achieve the effect of good application prospects and industrial production potential

Inactive Publication Date: 2016-03-09
甘肃皓骏药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] As mentioned above, a variety of methods for synthesizing indole compounds have been disclosed in the prior art. However, these existing methods have many defects such as low reaction yield, which affects the wide application in the field of pharmaceutical intermediate synthesis.

Method used

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  • Method for synthesizing diphenyl substituted indole compound
  • Method for synthesizing diphenyl substituted indole compound
  • Method for synthesizing diphenyl substituted indole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040]

[0041] In an appropriate amount of organic solvent (a mixture of 1,4-dioxane and DMSO (dimethyl sulfoxide) with a volume ratio of 1:2), add 100 mmol of the above formula (I) compound, 200 mmol of the above formula (II) Compound, 8mmol two-component catalyst (for 4mmol (A-taPhos) 2 PdCl 2 with 4mmolCu(TFA) 2 mixture), 5 mmol of the phosphine ligand L1 and 20 mmol of the acidic compound methanesulfonic acid; then the temperature was raised to 60°C with stirring, and the reaction was stirred at this temperature for 12 hours.

[0042] After the reaction, filter while it is hot, cool the filtrate naturally to room temperature, and adjust the pH to neutral, then fully shake and wash with deionized water, then add ethyl acetate to extract 2-3 times, combine the organic phases, and concentrate under reduced pressure. The concentrate was separated by silica gel column chromatography, washed with an acetone-chloroform mixture with a volume ratio of 1:2, so as to obtain the...

Embodiment 2

[0045]

[0046] In an appropriate amount of organic solvent (a mixture of 1,4-dioxane and DMSO (dimethyl sulfoxide) with a volume ratio of 1:2), add 100 mmol of the above formula (I) compound, 250 mmol of the above formula (II) Compound, 12.5mmol two-component catalyst (for 5mmol (A-taPhos) 2 PdCl 2 with 7.5mmolCu(TFA) 2 mixture), 7 mmol of phosphine ligand L1 and 25 mmol of acidic compound methanesulfonic acid; then the temperature was raised to 70°C with stirring, and the reaction was stirred at this temperature for 10 hours.

[0047] After the reaction, filter while it is hot, cool the filtrate naturally to room temperature, and adjust the pH to neutral, then fully shake and wash with deionized water, then add ethyl acetate to extract 2-3 times, combine the organic phases, and concentrate under reduced pressure. The concentrate was separated by silica gel column chromatography, washed with an acetone-chloroform mixture with a volume ratio of 1:2, so as to obtain the co...

Embodiment 3

[0049] Reaction formula is with embodiment 1, and concrete reaction process is as follows:

[0050] In an appropriate amount of organic solvent (a mixture of 1,4-dioxane and DMSO (dimethyl sulfoxide) with a volume ratio of 1:2), add 100 mmol of the above formula (I) compound, 300 mmol of the above formula (II) Compound, 15mmol two-component catalyst (for 5mmol (A-taPhos) 2 PdCl 2 with 10mmolCu(TFA) 2 mixture), 10 mmol of the phosphine ligand L1 and 30 mmol of the acidic compound methanesulfonic acid; then the temperature was raised to 80°C with stirring, and the reaction was stirred at this temperature for 8 hours.

[0051] After the reaction, filter while it is hot, cool the filtrate naturally to room temperature, and adjust the pH to neutral, then fully shake and wash with deionized water, then add ethyl acetate to extract 2-3 times, combine the organic phases, and concentrate under reduced pressure. The concentrate was separated by silica gel column chromatography, and w...

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Abstract

The invention relates to a method for synthesizing a diphenyl substituted indole compound which is represented as the following formula (III) and capable of being used as a medical intermediate. The method comprises the steps that the compounds in the following formula (I) and the following formula (II) are reacted in an organic solvent in the presence of bi-component catalysts, phosphine ligand and acid compounds so as to obtain the compound in the formula (III), wherein R1-R2 are H, C1-C6 alk yl or C1-C6 alkoxy, X is halogen and M is an alkali metal element. According to the method, appropriate substrates are selected, a unique catalyst, ligand, acid compound and organic solvent combined reaction system is used, and accordingly target products can be obtained in high yield, and the method has good application prospects and industrial production potentials in the technical field of medical intermediate synthesis.

Description

technical field [0001] The invention relates to a synthesis method of heterocyclic compounds, more particularly to a synthesis method of diphenyl-substituted indole compounds, and belongs to the field of synthesis of pharmaceutical intermediates. Background technique [0002] In the field of medicine, indole compounds are extremely important heterocyclic compounds, which have been widely used in the field of medicine because of their diverse biological activities, and many marketed drugs contain indole structures. [0003] It is precisely because of the important role of indole compounds that it is a very necessary task for pharmaceutical researchers to develop efficient synthesis methods for indole compounds. [0004] So far, many universities and research institutions have developed a variety of synthetic methods related to indole compounds, such as: [0005] RobertJ.Phipps et al. (“Cu(II)-CatalyzedDirectandSite-SelectiveArylationofIndolesUnderMildConditions”, J.Am.Chem.S...

Claims

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Application Information

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IPC IPC(8): C07D209/08
CPCC07D209/08
Inventor 张妍
Owner 甘肃皓骏药业有限公司
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