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Synthesis method of 6-chloroimidazo[1,2-a]pyridine-3-formonitrile

A synthetic method, 2-a technology, applied in the direction of organic chemistry, etc., can solve the problems of cumbersome operation, high impurity content, intense reaction, etc., and achieve the effect of high purity, mild reaction conditions, and easy operation

Inactive Publication Date: 2014-07-02
SHANDONG YOUBANG BIOCHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] 6-Chloro-imidazo[1,2-a]pyridine-3-carbonitrile is an important drug intermediate, the existing 6-chloro-imidazo[1,2-a]pyridine-3-carbonitrile During the preparation process, the reaction is intense, the operation is cumbersome, the impurity content in the product is high, and the yield is only about 40%. The above problems need to be improved

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Add 2-amino-5-chloropyridine (3.86g, 30mmol) and DMF-DMA (12mL) into a 50mL single-necked round-bottom flask, heat and stir the reaction, the reaction temperature is 100-110°C, the reaction is complete after 4h; rotary evaporation removes DMF-DMA, transferred to a 100mL flask without further treatment, directly added 30mL of DMF, 3.78g of sodium bicarbonate and 5.40g of bromoacetonitrile, heated and stirred for reaction, the reaction temperature was 130-140°C, and the reaction was terminated after 15h. Transfer the reaction mixture to a large beaker, add 200mL ethyl acetate, filter with suction, and wash the filter residue fully with ethyl acetate; add 150mL water to the filtrate for extraction, extract the aqueous phase with 200mL ethyl acetate, combine the organic phases, and add anhydrous sulfuric acid Sodium is fully dry. After suction filtration, ethyl acetate was removed by rotary evaporation to obtain a brown solid, which was recrystallized with absolute ethanol ...

Embodiment 2

[0018] Add 2-amino-5-chloropyridine (3.86g, 30mmol) and DMF-DMA (15mL) into a 50mL single-necked round bottom flask, heat and stir the reaction, the reaction temperature is 50-55°C, the reaction is complete after 3h; rotary evaporation removes DMF-DMA, transferred to a 100mL flask without further treatment, directly added 30mLDMA, 5.10g potassium bicarbonate and 6.12g bromoacetonitrile, heated and stirred for reaction, the reaction temperature was 50-55°C, and the reaction was terminated after 18h. Transfer the reaction mixture to a large beaker, add 200mL ethyl acetate, filter with suction, and wash the filter residue fully with ethyl acetate; add 150mL water to the filtrate for extraction, extract the aqueous phase with 200mL ethyl acetate, combine the organic phases, and add anhydrous sulfuric acid Sodium is fully dry. After suction filtration, ethyl acetate was removed by rotary evaporation to obtain a brown solid, which was recrystallized with absolute ethanol and ethyl a...

Embodiment 3

[0020] Add 2-amino-5-chloropyridine (38.6g, 300mmol) and DMF-DMA (120mL) into a 250mL single-necked round bottom flask, heat and stir the reaction, the reaction temperature is 100-110°C, the reaction is complete after 4h; rotary evaporation removes DMF-DMA, without further treatment, directly added 250mL of DMF, 37.8g of sodium bicarbonate and 54.0g of bromoacetonitrile, heated and stirred for reaction, the reaction temperature was 105-110°C, and the reaction was terminated after 16h. Transfer the reaction mixture to a large beaker, add 400 mL of ethyl acetate, filter with suction, and wash the filter residue with ethyl acetate; add 300 mL of water to the filtrate for extraction, extract the aqueous phase with ethyl acetate (2×300 mL), combine the organic phases, Add anhydrous sodium sulfate to fully dry. After suction filtration and rotary evaporation to remove ethyl acetate, a brown solid was obtained. The brown solid was recrystallized with absolute ethanol and ethyl acetat...

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Abstract

The invention relates to a synthesis method of 6-chloroimidazo[1,2-a]pyridine-3-formonitrile. The synthesis method of the 6-chloroimidazo[1,2-a]pyridine-3-formonitrile comprises the following steps: reacting 2-amino-5-chloropyridine and N,N-dimethylformamide dimethylacetal at a temperature ranging from 50 to 110 DEG C for 2-10 hours to obtain (E)-N'-(5-chloropyridine-2-yl)-N,N-dimethylformamidine, next, reacting (E)-N'-(5-chloropyridine-2-yl)-N,N-dimethylformamidine with bromoacetonitrile at a temperature ranging from 50 to 150 DEG C for 5-35 hours under the action of a base in a solvent, then carrying out ethyl acetate extraction, water washing, drying and rotary evaporation and concentration to obtain the coarse product of the 6-chloroimidazo[1,2-a]pyridine-3-formonitrile, and recrystallizing the coarse product solvent to obtain the pure product. The synthesis method of the 6-chloroimidazo[1,2-a]pyridine-3-formonitrile has the beneficial effects of mild reaction conditions, easiness for operation, stable product quality and high product purity.

Description

(1) Technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a synthesis method of 6-chloroimidazo[1,2-a]pyridine-3-carbonitrile. (2) Background technology [0002] 6-Chloro-imidazo[1,2-a]pyridine-3-carbonitrile is an important drug intermediate, the existing 6-chloro-imidazo[1,2-a]pyridine-3-carbonitrile In the preparation process, the reaction is intense, the operation is cumbersome, the impurity content in the product is high, and the yield is only about 40%. The above problems need to be improved. (3) Contents of the invention [0003] In order to make up for the deficiencies in the prior art, the present invention provides a synthetic method of 6-chloroimidazo[1,2-a]pyridine-3-carbonitrile, which is simple to operate and high in yield, and is suitable for laboratory and industrial production. [0004] The present invention is achieved through the following technical solutions: [0005] A kind of synthetic meth...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 李鑫樊红莉曹惊涛来新胜
Owner SHANDONG YOUBANG BIOCHEM TECH
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