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3-((4-chlorobenzene base) thio)-5-bromide-1-hydrogen-indole composite method

A synthetic method, the technology of chlorophenyl, which is applied in the field of synthesis of indole derivatives, can solve the problems of inability to convert technology into economic benefits, difficulty in expanding production scale, and difficulty in realizing large-scale reactions, so as to eliminate metal pollution , increase productivity, and expand the effect of production scale

Inactive Publication Date: 2014-12-24
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

First of all, the use of metals will not only cause great pollution to the environment, make the post-treatment of the reaction more complicated, but also increase the cost of the reaction; secondly, toxic solvents are volatile, and their use will not only cause great harm to the environment but also to people. health threats; reaction gas protection, harsh conditions, not easy to expand the scale of production
The above problems make it difficult to scale the reaction, apply it in actual production, and transform technology into economic benefits, which greatly reduces the significance of scientific research

Method used

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  • 3-((4-chlorobenzene base) thio)-5-bromide-1-hydrogen-indole composite method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Put 0.235mmol (0.046g) of 5-bromoindole and 0.940mmol (0.284g) of 4,4'-dichlorodiphenyl disulfide into a beaker, add 0.047mmol (0.012g) of tetra-n-butyl ammonium hydroxide, and then add Mixed solution of ethanol and water 21ml (V 乙醇 :V 水 = 1: 1.5) slightly heated and stirred, then the mixed solution was transferred to a 30ml stainless steel autoclave with a Teflon lining, heated to 130°C, and reacted for 48h under automatic pressure boosting, TLC tracking and determination of the disappearance of the reactant 5-bromoindole, Then it was naturally cooled to room temperature, and a yellow-brown solid was formed. The solid was collected by suction filtration, and the mother liquor was extracted with 170 ml of ethyl acetate. The organic layer was dried with anhydrous magnesium sulfate, and the solvent was evaporated to dryness to obtain a solid. The crude product is obtained by mixing the two solids. First pass through the column with petroleum ether with a boiling range o...

Embodiment 2

[0048] Put 3.760mmol (0.736g) of 5-bromoindole and 0.940mmol (0.284g) of 4,4'-dichlorodiphenyl disulfide into a beaker, add 0.752mmol (0.192g) of tetra-n-butyl ammonium hydroxide, and then add Mixed solution of ethanol and water 21ml (V 乙醇 :V 水 = 1: 1.5) slightly heated and stirred, then the mixed solution was transferred to a 30ml stainless steel autoclave with a Teflon lining, heated to 130°C, and reacted for 48h under automatic pressure boosting, TLC tracking and determination of the disappearance of the reactant 5-bromoindole, Then it was naturally cooled to room temperature, and a yellow-brown solid was formed. The solid was collected by suction filtration, and the mother liquor was extracted with 170 ml of ethyl acetate. The organic layer was dried with anhydrous magnesium sulfate, and the solvent was evaporated to dryness to obtain a solid. The crude product is obtained by mixing the two solids. First pass through the column with petroleum ether with a boiling range o...

Embodiment 3

[0050] Put 0.470mmol (0.092g) of 5-bromoindole and 0.940mmol (0.284g) of 4,4'-dichlorodiphenyl disulfide into a beaker, add 0.094mmol (0.024g) of tetra-n-butyl ammonium hydroxide, and then add Mixed solution of ethanol and water 21ml (V 乙醇 :V 水 = 1: 1.5) slightly heated and stirred, then the mixed solution was transferred to a 30ml stainless steel autoclave with a Teflon lining, heated to 130°C, and reacted for 48h under automatic pressure boosting, TLC tracking and determination of the disappearance of the reactant 5-bromoindole, Then it was naturally cooled to room temperature, and a yellow-brown solid was formed. The solid was collected by suction filtration, and the mother liquor was extracted with 170 ml of ethyl acetate. The organic layer was dried with anhydrous magnesium sulfate, and the solvent was evaporated to dryness to obtain a solid. The crude product is obtained by mixing the two solids. First pass through the column with petroleum ether with a boiling range o...

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Abstract

The invention provides a 3-((4-chlorobenzene base) thio)-5-bromide-1-hydrogen-indole composite method. 5-bromine indole and 4, 4 '-dichloro diphenyl disulfide ether serve as raw materials and are dissolved in an alcohol and water mixed solvent, an reaction is performed for 30 to 60 hours in the presence of strong base under the 80 to 140 DEG C and 5 to 15 pressure conditions, and the purified 3-((4-chlorobenzene base) thio)-5- bromide-1-hydrogen-indole is obtained through aftertreatment. According to the 3-((4-chlorobenzene base) thio)-5- bromide-1-hydrogen-indole composite method, the reaction conditions are mild, metal does not need to be added for metal catalysis in the reaction process, the gas protection is not required, and accordingly the difficulty of the treatment after the reaction is reduced, the reaction cost is greatly reduced, the pollution to the environment is reduced, and emissions of the waste are reduced.

Description

technical field [0001] The invention relates to a method for synthesizing indole derivatives, in particular to a method for synthesizing 3-((4-chlorophenyl)thio)-5-bromo-1-hydro-indole. Background technique [0002] Indole and its derivatives are biologically active substances, especially indole and its derivatives with 3-position sulfur arylation, which have strong biological activity and have a wide range of uses. First, they can be used as drug intermediates. Synthesis can treat such as Drugs for diseases such as heart disease, obesity, cancer, allergies, and bacterial infections; secondly, some 3-position sulfur arylated indole and its derivatives can even be directly used in medicine, such as cyclooxygenase inhibitors; In addition, the 3-position sulfur arylated indole and its derivatives also have certain applications in dyes and agricultural chemicals. [0003] The 3-position sulfur arylated indole and its derivatives are synthesized from indole and its derivatives w...

Claims

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Application Information

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IPC IPC(8): C07D209/30
CPCC07D209/30
Inventor 李新华赵龚明王宣令
Owner WENZHOU UNIVERSITY
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