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Method for synthesizing 5-bromo-7-azaindole

A kind of technology of azaindole and synthesis method, which is applied in the field of synthesis of 5-bromo-7-azaindole, can solve the problems of a large amount of bromine reaction process, long preparation route, difficult control, etc., and is suitable for large-scale industrial production , simple operation, less by-products

Inactive Publication Date: 2018-05-29
ITIC MEDCHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, there are mainly the following two methods for the synthesis of 5-bromo-7-azaindole: 1. Using 2-aminopyridine as a raw material, through bromination, coupling, and ring-closing synthesis, this method requires a large amount of bromine and the reaction process Difficult to control, low yield; 2, with 7-azaindole as raw material, through steps such as bromination reaction, elimination reaction, reduction reaction, oxidation reaction, make target product, this method preparation route is longer, complicated operation, low yield

Method used

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  • Method for synthesizing 5-bromo-7-azaindole

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Experimental program
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Effect test

Embodiment 1

[0020] A kind of synthetic method of 5-bromo-7-azaindole, comprises the following steps:

[0021] Dissolve 2-hydrazino-5-bromopyridine in the solvent, add concentrated sulfuric acid, stir and mix evenly, heat to a temperature of 70°C, add catalyst, add acetaldehyde under stirring condition, reflux for 3 hours, the reaction is completed, and lower to room temperature Afterwards, it is filtered, and the filtrate is distilled under reduced pressure and recrystallized to obtain 5-bromo-7-azaindole;

[0022] The catalyst is a mixture of phosphorus oxychloride, copper acetate and niobium pentachloride

[0023]

[0024] Catalyst is the mixture that the molar ratio of phosphorus oxychloride, copper acetate and niobium pentachloride is 4:3:1; Solvent is DMF or DMSO; The usage molar volume ratio of 2-hydrazino-5-bromopyridine and solvent is 2mol / L; the mass ratio of 2-hydrazino-5-bromopyridine to catalyst is 19:15; the molar ratio of 2-hydrazino-5-bromopyridine to acetaldehyde is 1:...

Embodiment 2

[0027] A kind of synthetic method of 5-bromo-7-azaindole, comprises the following steps:

[0028] Dissolve 2-hydrazino-5-bromopyridine in the solvent, add concentrated sulfuric acid, stir and mix evenly, heat to a temperature of 90°C, add catalyst, add acetaldehyde under stirring condition, reflux for 4 hours, the reaction is completed, and lower to room temperature Afterwards, it is filtered, and the filtrate is distilled under reduced pressure and recrystallized to obtain 5-bromo-7-azaindole;

[0029] The catalyst is a mixture of phosphorus oxychloride, copper acetate and niobium pentachloride

[0030]

[0031] Catalyst is the mixture that the molar ratio of phosphorus oxychloride, copper acetate and niobium pentachloride is 4:3:1; Solvent is DMF or DMSO; The usage molar volume ratio of 2-hydrazino-5-bromopyridine and solvent is 3mol / L; the mass ratio of 2-hydrazino-5-bromopyridine to catalyst is 19:18; the molar ratio of 2-hydrazino-5-bromopyridine to acetaldehyde is 1:...

Embodiment 3

[0034] A kind of synthetic method of 5-bromo-7-azaindole, comprises the following steps:

[0035] Dissolve 2-hydrazino-5-bromopyridine in a solvent, add concentrated sulfuric acid, stir and mix well, heat to a temperature of 70°C, add catalyst, add acetaldehyde under stirring condition, reflux for 4 hours, the reaction is completed, and lower to room temperature Afterwards, it is filtered, and the filtrate is distilled under reduced pressure and recrystallized to obtain 5-bromo-7-azaindole;

[0036] The catalyst is a mixture of phosphorus oxychloride, copper acetate and niobium pentachloride

[0037]

[0038] Catalyst is the mixture that the molar ratio of phosphorus oxychloride, copper acetate and niobium pentachloride is 4:3:1; Solvent is DMF or DMSO; The usage molar volume ratio of 2-hydrazino-5-bromopyridine and solvent is 2mol / L; the mass ratio of 2-hydrazino-5-bromopyridine to catalyst is 19:18; the molar ratio of 2-hydrazino-5-bromopyridine to acetaldehyde is 1:1.2;...

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Abstract

The invention discloses a method for synthesizing 5-bromo-7-azaindole. The method comprises dissolving 2-hydrazino-5-bromopyridine in a solvent, adding concentrated sulfuric acid into the solution, carrying out uniform mixing, heating the mixture to 70-90 DEG C, adding a catalyst into the mixed solution, adding acetaldehyde into the solution along with stirring, carrying out a reflux reaction process for 3-4h, then cooling the product to the room temperature, carrying out filtration, carrying out reduced pressure distillation on the filtrate and carrying out recrystallization to obtain 5-bromo-7-azaindole. The method has the advantages of simple processes, mild conditions, few by-products, high product purity and high product yield.

Description

technical field [0001] The invention relates to the field of pharmaceutical intermediates, in particular to a synthesis method of 5-bromo-7-azaindole. Background technique [0002] Indole compounds are an important branch of heterocyclic compounds, which have a variety of biological activities and are the most widely distributed heterocyclic compounds in nature. Indole compounds are important organic chemical raw materials and products, which can be used as intermediates of medicine, pesticides, dyes, spices and other fine chemical products, and have a wide range of applications in many fields. Azaindole can be regarded as the biological isostere of indole, so azaindole compounds play an important role in the design and synthesis of active pharmaceutical molecules. In terms of pharmacological effects, azaindole compounds have anti-cancer, anti-bacterial, anti-viral, and treatment of high blood pressure and other uses. Among them, 7-azaindole is an important compound in aza...

Claims

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Application Information

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IPC IPC(8): C07D209/08C07D471/04
CPCC07D209/08C07D471/04
Inventor 胡海威
Owner ITIC MEDCHEM CO LTD
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