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Synthetic method of 3,6-dichloroimidazo[1,2-a]pyridine

A technology of diclomidazole and its synthesis method, which is applied in the direction of organic chemistry, can solve the problems of unfavorable products and derivatives research and development, few preparation methods, etc., and achieve the effects of stable product quality, simple post-processing, and reasonable price

Inactive Publication Date: 2015-11-11
SHANDONG YOUBANG BIOCHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] Among these compounds, 3,6-dichloroimidazo[1,2-a]pyridine is an important intermediate in organic synthesis, mainly used in pharmaceutical intermediates, organic synthesis, and can also be used in pesticide production and spices, etc. , this preparation method is rarely documented, which is not conducive to the research and development of this product and its derivatives, and needs to be improved

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Add 2-amino-5-chloropyridine (12.86g, 100mmol), 40% aqueous solution of chloroacetaldehyde (17.66g, 90mmol), potassium bicarbonate (10g, 100mmol) and 80mL ( 62g) tert-butanol, start the magnetic stirrer, and the mixture in the reaction bottle was stirred and reacted at 75° C. for 8 hours. TLC detected that the reaction of the raw material 2-amino-5-chloropyridine was completed, N-chlorosuccinimide (16.02g, 120mmol) was added, heated in a water bath at 60°C and stirred for another 4 hours, TLC and GC were used to determine the intermediate 6 -Climidazo[1,2-a]pyridine reacts completely. Add water to the reaction solution, then suction filter the reaction solution, recrystallize the filter cake with ethyl acetate:n-hexane=1:3 to obtain the pure product 3,6-dichloroimidazo[1,2-a]pyridine, and use the filtrate Ethyl acetate extraction, rotary evaporation to remove the extractant to obtain the crude product, and then recrystallized with ethyl acetate: n-hexane = 1:3 to obtai...

Embodiment 2

[0027] Add 2-amino-5-chloropyridine (38.57g, 300mmol), 40% aqueous solution of chloroacetaldehyde (58.88g, 300mmol), potassium bicarbonate (30.00g, 300mmol) and 200mL (158g) acetonitrile, start the magnetic stirrer, the mixture in the reaction bottle was stirred and reacted at 75°C for 8 hours. TLC detected that the reaction of the raw material 2-amino-5-chloropyridine was completed, N-chlorosuccinimide (40.06g, 300mmol) was added, heated in a water bath at 60°C and stirred for another 4 hours, and intermediate 6 was determined by TLC and GC. -Climidazo[1,2-a]pyridine reacts completely. Add water to the reaction solution, then suction filter the reaction solution, recrystallize the filter cake with ethyl acetate:n-hexane=1:3 to obtain the pure product 3,6-dichloroimidazo[1,2-a]pyridine, and use the filtrate Ethyl acetate extraction, rotary evaporation to remove the extractant to obtain the crude product, and then recrystallization with ethyl acetate: n-hexane = 1:5 to obtain ...

Embodiment 3

[0029] Add 2-amino-5-chloropyridine (38.57g, 300mmol), 40% aqueous solution of chloroacetaldehyde (70.65g, 360mmol), sodium bicarbonate (30.2g, 360mmol) and 150mL (135 g) ethyl acetate, start the magnetic stirrer, and the mixture in the reaction bottle was stirred and reacted at 75° C. for 8 hours. TLC detected that the reaction of the raw material 2-amino-5-chloropyridine was completed, N-chlorosuccinimide (40.06g, 300mmol) was added, heated in a water bath at 60°C and stirred for another 4 hours, and intermediate 6 was determined by TLC and GC. -Climidazo[1,2-a]pyridine reacts completely. Add water to the reaction solution, then suction filter the reaction solution, recrystallize the filter cake with ethyl acetate:n-hexane=1:3 to obtain the pure product 3,6-dichloroimidazo[1,2-a]pyridine, and use the filtrate Ethyl acetate extraction, rotary evaporation to remove the extractant to obtain the crude product, and then recrystallized with ethyl acetate: n-hexane = 1:3 to obtain...

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Abstract

The invention belongs to the field of organic synthesis and in particular relates to a synthetic method of 3,6-dichloroimidazo[1,2-a]pyridine. The synthetic method comprises the following steps: by using 2-amino-5-chloropyridine, a chloroacetaldehyde water solution and N-chlorosuccinimide as raw materials, continuously reacting at 35-115 DEG C in proper solvents under the action of alkali to generate a crude product of 3,6-dichloroimidazo[1,2-a]pyridine and purifying the crude product, thus obtaining pure 3,6-dichloroimidazo[1,2-a]pyridine, wherein the ratio of amount of substance of 2-amino-5-chloropyridine and the chloroacetaldehyde water solution is 1 to (0.9-3.0), and the ratio of amount of substance of 2-amino-5-chloropyridine and N-chlorosuccinimide is 1 to (0.7-2.5). The synthetic method has the beneficial effects that the reaction raw materials are easier to obtain; the price is reasonable; the reaction conditions are mild; the synthetic method is easy to operate and control and is simple in after-treatment; the product has stable quality and high purity.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a synthesis method of 3,6-dichloroimidazo[1,2-a]pyridine. (1) Background technology [0002] On March 11, 2015, a preparation method of imidazopyridine derivatives was announced, the steps are as follows: [0003] (1) Synthesis of 5-fluoro-3-yl-N-methylpyrimidine-2-amine nitropyridine: [0004] Add 30g of 2-chloro-3-nitro-5-fluoropyridine to 260ml of acetonitrile, add 21g of potassium carbonate and 25g of methylamine hydrochloride, heat to reflux and stir overnight, add water and ethyl acetate to extract the liquid, and collect the filtrate. Concentration afforded 23 g of 5-fluoro-3-yl-N-methylpyrimidin-2-aminenitropyridine. [0005] (2) Synthesis of 5-fluoro-N2-methylpyridine-2,3-diamine: [0006] Add 22g of 5-fluoro-3-yl-N-methylpyrimidine-2-amine nitropyridine to 250ml of methanol, add 1.1g of 10% palladium carbon, feed hydrogen, stir at room temperature for 4 h...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 耿宣平樊红莉来新胜曹惊涛
Owner SHANDONG YOUBANG BIOCHEM TECH
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