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5-aza-indole preparation method

A technology of azaindole and nitropyridine nitrogen oxide, which is applied in the field of preparation of 5-azaindole, can solve the problems of incomplete reaction, lower reaction temperature, incomplete reaction, etc., and achieve rapid and mild reaction, color and luster Good, easy to recycle effect

Inactive Publication Date: 2006-02-08
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of this method is that methanol is produced, the boiling point is low, the reaction temperature is reduced, and the reaction is not complete; a large amount of Raney nickel catalyst is needed, and, no matter under pressure or normal pressure, the reaction is incomplete

Method used

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  • 5-aza-indole preparation method

Examples

Experimental program
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Effect test

Embodiment 1

[0020] The first step: 46.2 grams (0.3mol) of 3-methyl-4-nitropyridine nitrogen oxide, N, N-diethylformamide diethyl acetal 70ml, N, N-dimethylformamide 20ml Put it into a 1L four-neck flask, heat it slowly to 130°C under stirring conditions, react for 1.5 hours, distill off the ethanol generated in the reaction, and then recover the excess acetal and solvent N,N-dimethylacetamide under reduced pressure . The reddish-brown residue was dissolved in boiling ethanol, refrigerated overnight, and the precipitated solid was filtered by suction and dried to obtain purple-red crystal 3-dimethylaminovinyl-4-nitropyridine nitrogen oxide, which was dried and weighed 59.6g, with a yield of 95.1 %.

[0021] Step 2: Put 45g of 3-dimethylaminovinyl-4-nitropyridine nitrogen oxide, 2.7g of 10% palladium carbon, and 300ml of ethanol into a 500ml four-necked flask, cool it to 15°C in an ice bath, and start slowly dripping Add 35ml of 85% hydrazine hydrate, remove the ice bath after dropping, k...

Embodiment 2

[0024] Step 1: Replace N,N-dimethylformamide acetal with 65ml N,N-dimethylformamide acetal, 16ml N,N-dimethylformamide instead of N,N-dimethylformamide Formamide was slowly heated to 100°C under stirring conditions, and the rest were the same as in the first step of Example 1 to obtain purple-red crystal 3-dimethylamine vinyl-4-nitropyridine nitrogen oxide, which weighed 59.3g after drying. Yield 94.6%. ;

[0025] The second and third steps were the same as in Example 1 to obtain 21.8 g of 5-azaindole.

Embodiment 3

[0027] The first step is with embodiment 1;

[0028] Second step: replace hydrazine hydrate with 44g anhydrous ammonium formate, and mother liquor directly carries out next step reaction;

[0029] The third step is the same as in Example 1 to obtain 22.3g of 5-azaindole

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PUM

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Abstract

The invention provides a process for preparing 5-azaindole comprising the following steps, using 3-methyl-4-nitro pyridine nitrogen dioxide and N,N-dialkyl formamide dialkyl acetal as raw material for reacting 1-2 hrsa at 100-150 deg C, freezing and crystallizing to obtain 3-dialkylaminoacetylene-4-nitropyridine nitrogen dioxide, then deacidizing the nitro radicals into amino radicals with palladium-containing catalyst and hydrogen donor at 0 deg C to room temperature, then using Raney nickel and hydrogen donor as reducer for deoxidization and cyclization at 40-80 deg C.

Description

technical field [0001] The present invention relates to a preparation method of 5-azaindole. Background technique [0002] 5-Azaindole has a certain inhibitory effect on kinases and can be used to treat diseases such as cardiovascular disease, inflammation, central nervous system disorder and diabetes. 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 materials, at 120°C, React for 2 to 3 hours, distill to obtain 3-dimethylaminovinyl-4-nitropyridine nitrogen oxide, and then in a mixed solvent of ethanol and water, press 3-dimethylaminovinyl-4-nitropyridine nitrogen oxide In terms of oxides, 150% by weight of Raney nickel is used as a catalyst to carry out hydrogenation as a raw material to prepare 5-azaindole. The shortcoming of this method is to produce methyl alcohol, boiling point is low, has reduced reaction temperature, and reaction is not complete; Ne...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04C07D209/04C07D213/36
Inventor 戴立言姜昕鹏王晓钟陈英奇
Owner ZHEJIANG UNIV
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