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3-Iodo-6-chloro-imidazo [1,2-a] pyridine synthetic method

A synthesis method and chloroimidazole technology are applied in the field of synthesis of 3-iodo-6-chloroimidazo[1,2-a]pyridine, and can solve the problems of research and development of unfavorable products and derivatives, few preparation methods, etc. , to achieve the effect of stable product quality, simple post-processing and easy control

Inactive Publication Date: 2015-09-16
SHANDONG YOUBANG BIOCHEM TECH
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

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

Method used

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  • 3-Iodo-6-chloro-imidazo [1,2-a] pyridine synthetic method

Examples

Experimental program
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Effect test

Embodiment 1

[0027] Add 2-amino-5-chloropyridine (12.86g, 100mmol), 40% aqueous solution of chloroacetaldehyde (15.70g, 80mmol), potassium bicarbonate (10g, 100mmol) and 100mL ( 78.90 g) ethanol, start the magnetic stirrer, and the mixture in the reaction flask was stirred and reacted at 85° C. for 8 hours. TLC detected that the reaction of the raw material 2-amino-5-chloropyridine was completed, N-iodosuccinimide (22.50g, 100mmol) was added, and the reaction was continued for 7 hours under stirring. The intermediate 6-chloroimidazolo was determined by TLC and GC. [1,2-a]pyridine reacts to completion. The reaction solution was suction filtered, and the filter cake was recrystallized with ethyl acetate:n-hexane=1:3 to obtain the pure product 3-iodo-6-chloroimidazo[1,2-a]pyridine, and the filtrate was extracted with ethyl acetate, spin The extractant was evaporated to remove the crude product, and then recrystallized with ethyl acetate:n-hexane=1:3 to obtain the pure product 3-iodo-6-chloro...

Embodiment 2

[0029] Add 2-amino-5-chloropyridine (38.57g, 300mmol), 40% aqueous solution of chloroacetaldehyde (58.88g, 300mmol), potassium bicarbonate (30.00g, 300mmol) and 150mL (135g) ethyl acetate, start the magnetic stirrer, and the mixture in the reaction bottle was stirred and reacted at 85° C. for 8 hours. TLC detected the completion of the reaction of the raw material 2-amino-5-chloropyridine, added N-iodosuccinimide (67.49g, 300mmol), and reacted for another 7 hours under stirring. The intermediate 6-chloroimidazolo was determined by TLC and GC. [1,2-a]pyridine reacts to completion. The reaction solution was suction filtered, and the filter cake was recrystallized with ethyl acetate:n-hexane=1:3 to obtain the pure product 3-iodo-6-chloroimidazo[1,2-a]pyridine, and the filtrate was extracted with ethyl acetate, spin The extractant was evaporated to remove the crude product, and then recrystallized with ethyl acetate:n-hexane=1:3 to obtain the pure product 3-iodo-6-chloroimida...

Embodiment 3

[0031] Add 2-amino-5-chloropyridine (38.57g, 300mmol), 40% aqueous solution of chloroacetaldehyde (70.65g, 360mmol), sodium bicarbonate (30.2g, 360mmol) and 200mL (158g) acetonitrile, start the magnetic stirrer, and the mixture in the reaction flask was stirred and reacted at 85° C. for 8 hours. TLC detected that the reaction of the raw material 2-amino-5-chloropyridine was completed, N-iodosuccinimide (80.99g, 360mmol) was added, and the reaction was continued for 7 hours under stirring. The intermediate 6-chloroimidazolo was determined by TLC and GC. [1,2-a]pyridine reacts to completion. The reaction solution was suction filtered, and the filter cake was recrystallized with ethyl acetate:n-hexane=1:3 to obtain the pure product 3-iodo-6-chloroimidazo[1,2-a]pyridine, and the filtrate was extracted with ethyl acetate, spin The extractant was evaporated to remove the crude product, and then recrystallized with ethyl acetate:n-hexane=1:3 to obtain the pure product 3-iodo-6-chlor...

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Abstract

The present invention belongs to the field of organic synthesis, and in particular relates to a 3-iodo-6-chloro-imidazo [1,2-a] pyridine synthetic method. The synthetic method comprises the following steps: 2-amino-5-chloropyridine, A chloroacetaldehyde aqueous solution, and N-iodosuccinimide are used as raw materials for continuous reaction under the action of a base in a suitable solvent at 40-150 DEG C to obtain a 3-iodo-6-chloro-imidazo [1,2-a] pyridine crude product, wherein the ratio of the number of moles of 2-amino-5-chloropyridine to chloroacetaldehyde aqueous solution is 1: 0.7-2.8, the ratio of the number of moles of 2-amino-5-chloropyridine to N-iodosuccinimide is 1: 1.0-3.1, and the 3-iodo-6-chloro-imidazo [1,2-a] pyridine crude product is purified to obtain a 3-iodo-6-chloro-imidazo [ 1,2-a] pyridine pure product. Reaction raw materials are relatively easy to obtain, and are reasonable in prices, the reaction are mild in conditions, easy to operate, and easy to control, post-processing is simple, product quality is stable, and purity is high.

Description

(1) Technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a synthesis method of 3-iodo-6-chloroimidazo[1,2-a]pyridine. (2) 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 , concentrated to obtain 23g of 5-fluoro-3-yl-N-methylpyrimidin-2-amine nitropyridine. [0005] (2) Synthesis of 5-fluoro-N2-picoline-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, pass in hydrogen, stir at room temperature fo...

Claims

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Application Information

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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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