Preparation method of 6-azaindole

An azaindole, nitrogen technology, applied in the field of intermediate synthesis, can solve the problems of harsh anhydrous and oxygen-free conditions, unsuitable for industrialization, etc., and achieves the effects of simple reaction treatment, mild reaction conditions and high yield

Inactive Publication Date: 2022-01-28
ITIC MEDCHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

3. Using 2-chloro-4-methyl-5-aminopyridine as a raw material, the butyl lithium or LDA strong base reagent used in this method is harsh in anhydrous and oxygen-free conditions, and is not suitable for industrialization

Method used

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  • Preparation method of 6-azaindole
  • Preparation method of 6-azaindole
  • Preparation method of 6-azaindole

Examples

Experimental program
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Effect test

Embodiment 1

[0020] A preparation method of 6-azaindole, comprising the following steps:

[0021] Step 1. First prepare 4-(2-dimethylamino)ethylene-5-nitropyridine: add dry 290mL DMF to a 1L round bottom flask, then add 27.6g and 200mmol of 4-methyl-3- Nitropyridine and 2.76g of potassium carbonate, 26.6mL and 2.2 equivalents of dimethylformamide dimethyl acetal were added thereto under stirring; the mixture was heated to 85-95°C under a nitrogen atmosphere and stirred for 6 hours; the reaction When finished, the reaction was cooled to room temperature and the solution was poured into 500-700 mL of water; the dark orange-red suspension was filtered under vacuum, and the solid was collected and dried overnight in a vacuum oven to obtain 36.3 g of compound 4 with a yield of 94%. -(2-Dimethylamino)ethylene-5-nitropyridine;

[0022] Step 2. Dissolve 38.6g and 200mmol of the intermediate 4-(2-dimethylamino)ethylene-5-nitropyridine in 50% ethanol, add 3.0g and 600mmol of iron powder, and add th...

Embodiment 2

[0032] A preparation method of 6-azaindole, comprising the following steps:

[0033] Step 1. First prepare 4-(2-dimethylamino)ethylene-5-nitropyridine: add dry 290mL DMF to a 1L round bottom flask, then add 27.6g and 200mmol of 4-methyl-3- Nitropyridine and 2.76g of potassium carbonate, 26.6mL and 2.2 equivalents of dimethylformamide dimethyl acetal were added thereto under stirring; the mixture was heated to 85-95°C under a nitrogen atmosphere and stirred for 6 hours; the reaction When finished, the reaction was cooled to room temperature and the solution was poured into 500-700 mL of water; the dark orange-red suspension was filtered under vacuum, and the solid was collected and dried overnight in a vacuum oven to obtain 36.3 g of compound 4 with a yield of 94%. -(2-Dimethylamino)ethylene-5-nitropyridine;

[0034] Step 2. Dissolve 38.6g and 200mmol of the intermediate 4-(2-dimethylamino)ethylene-5-nitropyridine in 50% ethanol, add 3.0g and 600mmol of iron powder, and add th...

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Abstract

The invention discloses a preparation method of 6-azaindole, the preparation method comprises the following steps: step 1, firstly preparing 4-(2-dimethylamino) ethylene-5-nitropyridine, namely adding 290mL of dried DMF into a 1L round-bottom flask, then adding 27.6 g of 4-methyl-3-nitropyridine, 200mmol of 4-methyl-3-nitropyridine and 2.76 g of potassium carbonate, adding 26.6 mL of dimethylformamide dimethyl acetal with the equivalent weight of 2.2 into the mixed solution under the stirring condition; heating the mixture to 85-95 DEG C in a nitrogen atmosphere, and stirring for 6 hours; after the reaction is finished, cooling the reaction to room temperature, and pouring the solution into 500-700mL of water; and filtering the dark orange red suspension under a vacuum condition, collecting solids, and drying the solids in a vacuum oven overnight. According to the preparation method of the 6-azaindole, 4-methyl-2-nitropyridine is used as a raw material to be subjected to condensation reaction with DMF-DMA under the alkaline condition, then iron powder is used as a reducing agent to be subjected to ring closing under the acidic condition, the 6-azaindole is obtained, the reaction condition is mild, reaction treatment is simple, the yield is high, and the method is suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of intermediate synthesis, in particular to a preparation method of 6-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 medicines, pesticides, dyes, fragrances and other fine chemical products, and have a wide range of applications in many fields. Azaindole compounds can be regarded as bioisosteres of indole, so azaindole plays an important role in the design and synthesis of active pharmaceutical molecules. In terms of pharmacology, azaindole compounds have anticancer, antibacterial, antiviral, and treatment of high blood pressure and other purposes. 6-Azaindole is widely used in medicine and is an intermediate of antitum...

Claims

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Application Information

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