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Synthetic Technology of Heterocyclic Boronic Acid Compounds

A synthesis process and boronic acid technology are applied in the field of synthesis technology of heterocyclic boronic acids, which can solve problems such as inability to synthesize heterocyclic boronic acids, and achieve the effects of low toxicity, reduced harm, and high yield and purity.

Active Publication Date: 2017-01-04
上海泰坦科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In order to solve the problem that the boric acid pinacol ester synthesis process existing in the above-mentioned prior art cannot synthesize heterocyclic boronic acid compounds such as 7-azaindole-5-boronic acid pinacol ester, 7-azaindole-4-boronic acid pinacol Alcohol ester, the technical problem of 7-azaindole-3-boronic acid pinacol ester, after the inventor has carried out a large amount of in-depth studies, thus has completed the present invention

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] This embodiment relates to a synthesis process of heterocyclic boronic acid compounds, comprising the following steps:

[0018] Step 1, add triethylamine (0.20mol) to a solution of 5-chloro-7-azaindole (3g, 0.02mol) in dichloromethane (50ml) at 0-5°C, and then add dropwise under stirring Contain the dichloromethane (100ml) solution of tert-butyldimethylsilyl chloride (0.2mol), then stir the reaction at room temperature overnight until TLC shows that the reaction is complete, add 50ml of water and 10ml of 0.1mol / L dilute hydrochloric acid after the reaction is complete, and divide After the layer, the dichloromethane phase was washed successively with 50ml of water, 50ml of saturated sodium carbonate solution and 50ml of saturated sodium chloride, then the solvent was evaporated, washed with acetone three times and then dried to obtain a yellow solid;

[0019] Step 2, the above-mentioned yellow solid was dissolved in 50ml THF, and 0.005mol sodium carbonate (0.53g) was ad...

Embodiment 2

[0024] This embodiment relates to a synthesis process of heterocyclic boronic acid compounds, comprising the following steps:

[0025] Step 1, add triethylamine (0.20mol) to a solution of 5-chloro-7-azaindole (3g, 0.02mol) in dichloromethane (50ml) at 0-5°C, then add dropwise under stirring Contain the dichloromethane (100ml) solution of tert-butyldimethylsilyl chloride (0.2mol), then stir the reaction at room temperature overnight until TLC shows that the reaction is complete, add 50ml of water and 10ml of 0.1mol / L dilute hydrochloric acid after the reaction is complete, and divide After the layer, the dichloromethane phase was washed successively with 50ml of water, 50ml of saturated sodium carbonate solution and 50ml of saturated sodium chloride, then the solvent was evaporated, washed with acetone three times and then dried to obtain a yellow solid;

[0026] Step 2, dissolve the above yellow solid in 50ml THF, add 0.005mol sodium carbonate (0.53g) while keeping the tempera...

Embodiment 3

[0031] This embodiment relates to a synthesis process of heterocyclic boronic acid compounds, comprising the following steps:

[0032] Step 1, add triethylamine (0.20mol) to a solution of 5-chloro-7-azaindole (3g, 0.02mol) in dichloromethane (50ml) at 0-5°C, and then add dropwise under stirring Contain the dichloromethane (100ml) solution of tert-butyldimethylsilyl chloride (0.2mol), then stir the reaction at room temperature overnight until TLC shows that the reaction is complete, add 50ml of water and 10ml of 0.1mol / L dilute hydrochloric acid after the reaction is complete, and divide After the layer, the dichloromethane phase was washed successively with 50ml of water, 50ml of saturated sodium carbonate solution and 50ml of saturated sodium chloride, then the solvent was evaporated, washed with acetone three times and then dried to obtain a yellow solid;

[0033] Step 2, the above-mentioned yellow solid was dissolved in 50ml THF, and 0.005mol sodium carbonate (0.53g) was adde...

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Abstract

The invention relates to a synthetic process of a heterocyclic boric acid compound. The process comprises the following steps: carrying out reaction on 5-chloro-7-azaindole and tert-butyldimethylsilyl chloride in the presence of triethylamine to carry out posttreatment to obtain a yellow solid; carrying out reaction on yellow solid and trimethyl borate in the presence of sodium carbonate to carry out post-treatment to obtain a yellow oily object; carrying out reaction on the yellow oily object and pinacol and concentrating to obtain a colorless oily object; and carrying out posttreatment on the colorless oily object to obtain a white solid to obtain 7-azaindole-pinacol boronate. Not only is the synthetic method provided by the invention yield and high in purity, but also the toxicity of the used chemical reagent is less, so that the damage on the operator is reduced, thereby facilitating industrial scaled production. The synthetic method is also suitable for synthesizing other heterocyclic boric acid compounds such as 7-azaindole-4-pinacol boronate, 7-azaindole-3-pinacol boronate and has an important application value.

Description

technical field [0001] The invention relates to a synthesis process of heterocyclic compounds, in particular to a synthesis process of heterocyclic boronic acid compounds. Background technique [0002] Nitrogen-containing heterocyclic boronic acids and their esters can be used in the design of a series of new drug synthesis and the establishment of high-throughput screening compound libraries. Status, especially in biomedicine, heterocyclic boronic acid compounds can not only be used as enzyme inhibitors for the treatment of diseases such as tumors and microbial infections, but also as fluorescent probes for identifying hydrogen peroxide, sugars, copper ions, Fluorescent probes for fluoride ions and catecholamines, etc., therefore, to study the synthesis process of heterocyclic boronic acid compounds such as 7-azaindole-5-boronic acid pinacol ester, 7-azaindole-4- The synthesis technology of boric acid pinacol ester and 7-azaindole-3-boric acid pinacol ester has important a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02
CPCC07F5/04
Inventor 谢应波张庆张华徐肖冰张维燕罗桂云
Owner 上海泰坦科技股份有限公司
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