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A kind of synthetic method of 5 azaindole

An azaindole and a synthesis method technology are applied in the field of 5-azaindole synthesis, can solve the problems of high synthesis cost, long reaction time, low reaction efficiency and the like, and achieve lower synthesis cost, high controllability and optimization. The effect of the reaction process

Inactive Publication Date: 2017-10-13
ITIC MEDCHEM CO LTD
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Problems solved by technology

[0005] The second is to start from 4-amino-3-bromopyridine, undergo palladium-catalyzed Stille reaction, and then form a ring under acidic conditions to generate 5-azaindole, but the reaction time is long, the yield is low, and the synthesis cost is high
However, the reduction system composed of iron powder and acetic acid has poor stability, and needs to increase the temperature to achieve a better reduction effect, resulting in high energy consumption and low reaction efficiency.

Method used

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  • A kind of synthetic method of 5 azaindole
  • A kind of synthetic method of 5 azaindole
  • A kind of synthetic method of 5 azaindole

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Embodiment 1

[0040] A kind of synthetic method of 5-azaindole, take 3-methyl-4-nitropyridine oxynitride as starting raw material, first generate enamine, then undergo reduction reaction, generate 5-azaindole, comprise the following Steps:

[0041] Step 1: Add 3.08g of 3-methyl-4-nitropyridine nitrogen oxide, 12mL of DMF, and 10mL of DMA into a 100mL round-bottomed flask in sequence, place in an oil bath, heat up to 110°C, and reflux for 20 minutes; After the reaction solution was cooled, the solvent was distilled off under reduced pressure, 10 mL of absolute ethanol was added, filtered with suction, and the solid was washed and dried to obtain 3-dimethylaminovinyl-4-nitropyridine nitrogen oxide;

[0042] The second step: add 3.00g of 3-dimethylaminovinyl-4-nitropyridine nitrogen oxide and 30mL of copper sulfate aqueous solution (mass concentration is 5%) in a 100mL pear-shaped flask, and add 1g of zinc powder under stirring at room temperature ; The temperature was raised to 50°C, and the...

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Abstract

The invention discloses a synthesizing method of 5-azaindole. The synthesizing method is characterized in that 3-methyl-4-nitropyridine-1-oxide is used as initial raw material to produce enamine, and reduction by a zinc / copper sulfate aqueous solution system is performed to synthesize the 5-azaindole. The synthesizing method has the advantages that the reaction time is shortened, the reaction process is stable, high yield is achieved, cost is lowered, and high economic benefit is achieved.

Description

Technical field: [0001] The invention relates to a synthesis method of 5-azaindole, which belongs to the field of chemical synthesis. Background technique: [0002] Azaindole is an important intermediate of fine chemical products. It has a wide range of applications in the fields of medicine, food, pesticides, and daily chemicals. The synthesis of indole derivatives is also a hot spot in the field of organic chemistry. Although there have been many efficient methods for synthesizing indole derivatives, some classic methods for synthesizing indole are not very suitable for the synthesis of azaindole because azaindole is structurally different from indole. Among the azaindole compounds, 5-azaindole is more difficult to synthesize, and many classic methods for synthesizing indole rings and methods for synthesizing other azaindoles cannot synthesize 5-azaindole well. Therefore, it is necessary to study the synthesis method of 5-azaindole. [0003] At present, there are mainly ...

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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