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A kind of synthetic method of 5-bromo-7-azaindole

A kind of technology of azaindole and synthesis method, applied in the field of synthesis of 5-bromo-7-azaindole, can solve the problems of long reaction time, low economic benefit, complicated reaction operation, etc., achieve shortening the time of reaction, Optimized reaction conditions and high reaction selectivity

Inactive Publication Date: 2017-10-13
ITIC MEDCHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Optimum process conditions: ① hydrogenation reduction, reaction pressure is 4MPa, reaction temperature is 95°C, reaction time is 12h, bromination, the molar ratio of 7-azaindoline and bromine is 1: 1.15, and the total yield is 74.7% , this method is fast and simple, but its reaction time is long, the reaction operation is complicated, and the economic benefit is low

Method used

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  • A kind of synthetic method of 5-bromo-7-azaindole
  • A kind of synthetic method of 5-bromo-7-azaindole
  • A kind of synthetic method of 5-bromo-7-azaindole

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Effect test

Embodiment 1

[0075] A synthetic method of 5-bromo-7-azaindole, comprising the following steps:

[0076] The first step: synthesis of 7-azaindoline:

[0077] Add 30g of 7-azaindole and 5g of platinum carbon catalyst (3% Pt content) into the pressure reactor, add 250mL of cyclohexane as a solvent, fill in 2MPa hydrogen with stirring, raise the temperature to 90°C, and react for 5h ;

[0078] After cooling and filtering, the filter cake was washed twice with cyclohexane, the filtrate was combined, the solvent was concentrated and evaporated to dryness to obtain 7-azaindoline;

[0079] The reaction in this step is a light-avoiding reaction;

[0080] The second step: Synthesis of 5-bromo-7-azaindoline:

[0081] Add the 7-azaindoline, 300mL of dichloromethane, and 3g of sodium bromide synthesized in the first step above into a 1L round-bottomed flask, mix and stir, add 48g of bromine dropwise at room temperature, and finish the dropwise addition in 30 minutes. After the addition, the tempera...

Embodiment 2

[0088] A synthetic method of 5-bromo-7-azaindole, comprising the following steps:

[0089] The first step: synthesis of 7-azaindoline:

[0090] Add 30g of 7-azaindole and 10g of platinum carbon catalyst (5% Pt content) into the pressure reactor, add 250mL of cyclohexane as a solvent, fill with 3MPa hydrogen under stirring, raise the temperature to 95°C, and react for 8h ;

[0091] After cooling and filtering, the filter cake was washed twice with cyclohexane, the filtrate was combined, the solvent was concentrated and evaporated to dryness to obtain 7-azaindoline;

[0092] The reaction in this step is a light-avoiding reaction;

[0093] The second step: Synthesis of 5-bromo-7-azaindoline:

[0094] Add the 7-azaindoline, 300mL of dichloromethane, and 4g of sodium bromide synthesized in the first step above into a 1L round-bottomed flask, mix and stir, add 50g of bromine dropwise at room temperature, and finish the dropwise addition in 30 minutes. After the addition, the tem...

Embodiment 3

[0101] A synthetic method of 5-bromo-7-azaindole, comprising the following steps:

[0102] The first step: synthesis of 7-azaindoline:

[0103] 30g of 7-azaindole and 5g of platinum carbon catalyst (5% Pt content) were added to the pressure reactor, 250mL of cyclohexane was added as a solvent, and 2-3MPa hydrogen gas was charged under stirring, and the temperature was raised to 90°C. Reaction 8h;

[0104] After cooling and filtering, the filter cake was washed twice with cyclohexane, the filtrate was combined, the solvent was concentrated and evaporated to dryness to obtain 7-azaindoline;

[0105] The reaction in this step is a light-avoiding reaction;

[0106] The second step: Synthesis of 5-bromo-7-azaindoline:

[0107] Add 7-azaindoline, 300mL of dichloromethane, and 3g of sodium bromide synthesized in the first step above into a 1L round-bottomed flask, mix and stir, and add 50g of bromine dropwise at room temperature, and the dropwise addition is completed in 30 minute...

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Abstract

The invention discloses a synthesis method of 5-bromo-7-azaindole. With 7-azaindole as the raw material, hydrogenation reduction, bromination and dehydrogenation are conducted, a platinum-carbon catalyst is added for catalyzing 7-azaindole to conduct hydrogenation to prepare dihydro-7-azaindole, catalysis efficiency is improved, and reaction energy consumption and reaction time are decreased; 5-bromo-7-azaindoline is synthesized by adding sodium bromide for catalysis, a mixture of chromic oxide, zinc oxide and magnesium oxide is added for substituting manganese dioxide for catalytic dehydrogenation reaction, reaction time can be effectively shortened, and reaction yield is increased. By means of the method, reaction efficiency can be effectively improved, reaction time is shortened, the total reaction yield is increased, process waste liquid and waste slag are reduced, industrial popularization is facilitated, and extremely high economic benefits are achieved.

Description

Technical field: [0001] The invention relates to a synthesis method of 5-bromo-7-azaindole, which belongs to the field of chemical synthesis. Background technique: [0002] 7-Azaindole is an important class of heterocyclic compounds, which are similar in structure to indole and purine. Its derivatives have the activity of inhibiting various proteases, so they have potential biological and medicinal value, so they are widely used in medicine widely used in research. 5-bromo-7-azaindole is an important intermediate of antineoplastic drugs, although there are reports on the synthesis methods of multiple azaindole and derivatives thereof, so far, 5-bromo-7-azaindole Synthetic bibliographical reports of synthetic 5-bromo-7-azaindole mainly contain the following methods both at home and abroad at present: [0003] It is made from 2-aminopyridine through bromination, coupling and ring closure. This route is complicated to operate, needs to use bromine in a large amount, and reac...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 丁靓胡海威闫永平
Owner ITIC MEDCHEM CO LTD
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