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5-azaindole preparation method

The technology of an azaindole and a production method is applied in the field of preparing 5-azaindole, can solve the problems such as inability to apply enlarged production, low reaction temperature, etc., and achieves low production cost, mild chemical reaction conditions, and strong operability. Effect

Inactive Publication Date: 2013-12-04
ASCEPION PHARMA
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Problems solved by technology

The disadvantage of this method is that it requires a very low reaction temperature, reaching minus 40°C, and it needs to use a very flammable n-butyllithium solution. These two disadvantages make this method cannot be applied to scale-up production

Method used

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Embodiment Construction

[0024] The present invention will be described in detail below through specific embodiments, but the present invention is not limited to these examples.

[0025] Preparation of 3-picoline nitrogen oxide: 3-picoline (188.3g, 2.0mol) was added to 800ml of glacial acetic acid, and under stirring, 350ml of 35% hydrogen peroxide was slowly added dropwise to the reactor. After the dropwise addition, the mixture was heated to 80° C., and after 7 hours of reaction, glacial acetic acid and excess hydrogen peroxide were removed by rotary evaporation to obtain 220 g of crude 3-picoline nitrogen oxide. It was used directly in the next step without purification.

[0026] Preparation of 3-methyl-4-nitropyridine nitrogen oxide: below 20°C, slowly drop 500ml of nitric acid into 650ml of concentrated sulfuric acid to prepare the mixed acid required for the reaction. Add 3-picoline nitrogen oxide (220 g, 2.0 mol) dropwise to the mixed acid prepared above, and control the dropping rate so that ...

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Abstract

The present invention discloses a 5-azaindole preparation method, wherein 3-methylpyridine is adopted as a raw material, and the 5-azaindole preparation method comprises the following five steps that: (1) 3-methylpyridine is subjected to an oxidation reaction under an oxidant effect to obtain a 3-methylpyridine nitrogen oxide, (2) the 3-methylpyridine nitrogen oxide is subjected to a nitration reaction under a mixed acid effect to obtain a 3-methyl-4-nitropyridine nitrogen oxide, (3) the 3-methyl-4-nitropyridine nitrogen oxide and phosphorus trichloride are subjected to a reaction in a solvent to obtain 3-methyl-4-nitropyridine, (4) the 3-methyl-4-nitropyridine and N,N-dimethyl formamide dialkyl acetal are subjected to a reaction in a solvent N,N-dimethyl formamide under a heating condition to obtain 3-dialkylamine vinyl-4-nitropyridine, and (5) the 3-dialkylamine vinyl-4-nitropyridine is subjected to a reduction reaction under a metal catalyst effect while ring closure is performed to obtain the final product 5-azaindole.

Description

technical field [0001] The invention relates to a method for preparing 5-azaindole by using 3-picoline as raw material. Background technique [0002] 5-Azaindole is an increasingly important pharmaceutical intermediate. Its structural formula is: [0003] [0004] Studies have found that 5-azaindole is a very valuable intermediate in the synthesis of some biologically active compounds. In addition, 5-azaindole has a certain inhibitory effect on kinases and can be used to treat diseases such as cardiovascular diseases, inflammation, central nervous system disorders and diabetes. [0005] For example, it was reported in the document Chimie Therapeutique, 5, 559-566 (1973) that 5-azaindole can be synthesized to obtain 4-arylamino-5-azaindole compounds, which have anti-inflammatory effects. [0006] U.S. Patent No. 4,625,033 discloses a preparation method of 5-azaindole: using 3-methyl-4-nitropyridine nitrogen oxide and N,N-dimethylformamide dimethyl acetal as raw material...

Claims

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Application Information

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IPC IPC(8): C07D471/04
Inventor 高小勇
Owner ASCEPION PHARMA
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