Method for synthetizing 6-bromine imidazo [1, 2-alpha] pyridine-3-carbonitrile

A synthesis method, 2-a technology, applied in organic chemistry and other directions, can solve the problems of intense reaction, complicated operation, high impurity content, and achieve the effects of easy operation, high purity and mild reaction conditions

Inactive Publication Date: 2014-06-25
SHANDONG YOUBANG BIOCHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] 6-bromo-imidazo[1,2-a]pyridine-3-carbonitrile is an important drug intermediate, the existing 6-bromo-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-bromopyridine (5.19g, 30mmol) and DMF-DMA (16mL) into a 50mL single-necked round-bottom flask, heat and stir the reaction, the reaction temperature is 50-55°C, the reaction is completed 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 50-55°C, and the reaction was terminated after 16h. 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 ...

Embodiment 2

[0018] Add 2-amino-5-bromopyridine (5.19g, 30mmol) and DMF-DMA (18mL) into a 50mL single-necked round bottom flask, heat and stir the reaction, the reaction temperature is 100-105°C, the reaction is completed after 3.5h; rotary evaporation DMF-DMA was removed and transferred to a 100mL flask without further treatment. Directly add 30mLDMA, 5.10g potassium bicarbonate and 6.12g bromoacetonitrile and heat and stir the reaction. The reaction temperature is 140-145°C, and the reaction ends 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. Ethyl acetate was removed by rotary evaporation after suction filtration to obtain a brown solid, which was recrystallized with absolute ethanol and ethyl acet...

Embodiment 3

[0020] Add 2-amino-5-bromopyridine (51.9g, 300mmol) and DMF-DMA (150mL) 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 100-110°C, and the reaction was terminated after 15h. 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, ethyl acetate was removed by rotary evaporation to obtain a brown solid, which was recrystallized with absolute ethanol and ethyl acetate / n-hexane 1:...

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Abstract

The invention relates to a method for synthetizing 6-bromine imidazo [1, 2-alpha] pyridine-3-carbonitrile. The method for synthetizing the 6-bromine imidazo [1, 2-alpha] pyridine-3-carbonitrile comprises the following steps: reacting 2-amino-5-bromopyridine with N, N-dimethylformamide dimethyl acetal for 2-10 hours at the temperature of 50-110 DEG C to obtain (E)-N'-(5-bromopyridine-2-yl)-N, N-dimethyl formamidine; in a solvent, reacting (E)-N'-(5-bromopyridine-2-yl)-N, N-dimethyl formamidine with bromoacetonitrile for 5-35 hours at the temperature of 50-150 DEG C under the action of alkali, carrying out ethyl acetate extraction, washing, drying, rotary evaporation and concentration to obtain a crude product of 6- bromine imidazo [1, 2-alpha] pyridine-3-carbonitrile, recrystallizing the crude product by using a solvent to obtain a pure product. The method disclosed by the invention has the beneficial effects that the reaction is mild in condition and easy to operate and the product is stable in quality and high in 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-bromoimidazo[1,2-a]pyridine-3-carbonitrile. (2) Background technology [0002] 6-bromo-imidazo[1,2-a]pyridine-3-carbonitrile is an important drug intermediate, the existing 6-bromo-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 of the prior art, the present invention provides a synthetic method of 6-bromoimidazo[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 method o...

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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