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Synthesis method of 5-chloro-7-azaindole

The technology of azaindole and synthesis method is applied in the field of synthesis of 5-chloro-7-azaindole, which can solve the problems of low yield and insufficient mild conditions, and achieve good compatibility, mild conditions, The effect of high yield

Inactive Publication Date: 2017-01-04
叶芳
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this preparation method requires high temperature and high pressure, the conditions are not mild enough, and the yield is not high

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Synthesize 5-chloro-7-azaindole according to the following steps:

[0026] (1) Clean the 250mL three-neck bottle and fill it with nitrogen for 2 hours, add dilithium initiator under nitrogen gas, then add trimethylbromosilane dropwise, the molar ratio of dilithium initiator to trimethylbromosilane is 0.9 : 1, the temperature was controlled to be 10° C. and stirred and reacted for 3 hours, washed with deionized water to neutrality after taking out, and obtained silicon-containing organolithium after vacuum drying at room temperature for 2 hours;

[0027] (2) Add 2-amino-3-picoline into ethanol, stir until completely dissolved, add triethylamine, add di-tert-butyl dicarbonate dropwise within 30 minutes at room temperature, evaporate ethanol after 20 hours of reaction, and After adding distilled water, the product was extracted 3 times with methyl acetate, the combined extracts were washed repeatedly with sodium chloride, then dried with sodium sulfate, concentrated and re...

Embodiment 2

[0033] Synthesize 5-chloro-7-azaindole according to the following steps:

[0034] (1) Clean the 250mL three-neck bottle and fill it with nitrogen for 2 hours, add dilithium initiator under nitrogen gas, then add trimethylbromosilane dropwise, the molar ratio of dilithium initiator to trimethylbromosilane is 0.92 : 1, the temperature was controlled to be 10° C. and stirred and reacted for 3 hours, washed with deionized water to neutrality after taking out, and obtained silicon-containing organolithium after vacuum drying at room temperature for 2 hours;

[0035] (2) Add 2-amino-3-picoline into ethanol, stir until completely dissolved, add triethylamine, add di-tert-butyl dicarbonate dropwise within 30 minutes at room temperature, evaporate ethanol after 20 hours of reaction, and After adding distilled water, the product was extracted 3 times with methyl acetate, the combined extracts were washed repeatedly with sodium chloride, then dried with sodium sulfate, concentrated and r...

Embodiment 3

[0041] Synthesize 5-chloro-7-azaindole according to the following steps:

[0042] (1) Clean the 250mL there-necked bottle and fill it with nitrogen for 2 hours, add the dilithium initiator under the nitrogen gas condition, then add trimethylbromosilane dropwise, the molar ratio of dilithium initiator to trimethylbromosilane is 0.94 : 1, the temperature was controlled to be 10° C. and stirred and reacted for 3 hours, washed with deionized water to neutrality after taking out, and obtained silicon-containing organolithium after vacuum drying at room temperature for 2 hours;

[0043] (2) Add 2-amino-3-picoline into ethanol, stir until completely dissolved, add triethylamine, add di-tert-butyl dicarbonate dropwise within 30 minutes at room temperature, evaporate ethanol after 20 hours of reaction, and After adding distilled water, the product was extracted 3 times with methyl acetate, the combined extracts were washed repeatedly with sodium chloride, then dried with sodium sulfate...

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Abstract

The invention provides a synthesis method of 5-chloro-7-azaindole. The synthesis method comprises the following steps: (1) reacting a dilithium initiator and trimethylbromosilane to prepare silicon-containing organic lithium; (2) reacting 2-amino-3-methylpyridine and di-tert-butyl dicarbonate to prepare 2-N-BOC-amino-3-methylpyridine; (3) performing lithiation on the 2-N-BOC-amino-3-methylpyridine through the silicon-containing organic lithium, and performing delithiation activation, cyclization and dehydration to prepare 7-azaindole; (4) performing hydrogenation reduction reaction on the 7-azaindole to generate 2,3-dihydro-7-azaindole; (5) performing chlorination reaction on the 2,3-dihydro-7-azaindole through liquid chlorine to generate 5-chloro-2,3-dihydro-7-azaindole; and (6) performing dehydrogenation reaction on the 5-chloro-2,3-dihydro-7-azaindole to obtain 5-chloro-7-azaindole. The synthesis method provided by the invention has the advantages of mild conditions and high yield.

Description

technical field [0001] The invention relates to the field of pharmaceutical intermediates, in particular to a synthesis method of 5-chloro-7-azaindole. Background technique [0002] 7-Azaindole is an important class of heterocyclic compounds. It is similar in structure to indole and purine. It is the biological isostere of indole and has special biological activity. Its derivatives have the ability to inhibit various proteases. It has shown potential medicinal value in antihistamine and antidopamine, and has attracted more and more attention from researchers. 7-Azaindole derivatives can be used to treat various diseases such as cardiovascular diseases, tumors, diabetes and cancer, among which 5-chloro-7-azaindole is commonly used in the synthesis of new anti-tumor drugs-protease inhibitors intermediates. [0003] The publication number is CN101402635B, the publication date is 2011.01.12, and the applicant is the Chinese patent of Yaben Chemical (Suzhou) Co., Ltd., which di...

Claims

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Application Information

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IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 叶芳
Owner 叶芳
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