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Synthetic method of ethyl 3-aldehyde-6-chloroimidazo[1,2-a]pyridine-8-formate

A technology of ethyl formate and synthesis method, which is applied in the direction of organic chemistry, can solve the problems of lack of literature and patent reports, high market price, and difficult synthesis, and achieve the effects of stable product quality, easy operation, and simple post-processing

Inactive Publication Date: 2015-03-11
SHANDONG YOUBANG BIOCHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This product is a novel pharmaceutical intermediate with great medical value, but its synthesis is difficult, the market price is expensive, and there is a lack of literature and related patent reports

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] 100mmol (16.6g) of ethyl 2-aminonicotinate was reacted with 110mmol (14.69g) of N-chlorosuccinimide in 200ml of acetonitrile for three hours at room temperature. After the reaction was completed, it was placed in an environment of zero degrees Celsius for three hours, filtered with suction, and the filter cake was rinsed with acetonitrile to obtain 24.1 g of solid, with a yield of 98.36%. Acetonitrile was recovered by rotary evaporation.

[0020] Take 2-amino-5-chloronicotinic acid ethyl ester (10g, 50mmol) solid in a 250ml one-necked flask, add 100mL N,N-dimethylformamide dimethyl acetal, react at 60°C for 5 hours, and react Complete the preparation of N,N-dimethyl-N'-2-(3-ethylformate-5-chloro-pyridinyl)-formamidine intermediate, and remove excess N,N-dimethylformamide by rotary evaporation Dimethyl acetal, add 40% chloroacetaldehyde aqueous solution (12.76g, chloroacetaldehyde 65mmol), react at 0°C for 10 hours, after the reaction is completed, cool to room tempera...

Embodiment 2

[0022] 100mmol (16.6g) of ethyl 2-aminonicotinate was reacted with 110mmol (14.69g) of N-chlorosuccinimide in 200ml of acetonitrile for three hours at room temperature. After the reaction was completed, it was placed in an environment of zero degrees Celsius for three hours, filtered with suction, and the filter cake was rinsed with acetonitrile to obtain 24.0 g of solids, with a yield of 97.9%. Acetonitrile was recovered by rotary evaporation.

[0023] Take 2-amino-5-chloronicotinic acid ethyl ester (10g, 50mmol) solid in a 250ml single-necked flask, add 100mL of N,N-dimethylformamide dimethyl acetal, and react at 100°C for 5 hours. Complete the preparation of N,N-dimethyl-N'-2-(3-ethylformate-5-chloro-pyridinyl)-formamidine intermediate, and remove excess N,N-dimethylformamide by rotary evaporation Dimethyl acetal, add 40% chloroacetaldehyde aqueous solution (14.72g, chloroacetaldehyde 75mmol), react at 60°C for 15 hours, after the reaction is completed, cool to room temper...

Embodiment 3

[0025] 100mmol (16.6g) of ethyl 2-aminonicotinate was reacted with 110mmol (14.69g) of N-chlorosuccinimide in 200ml of acetonitrile for three hours at room temperature. After the reaction was completed, it was placed in an environment of zero degrees Celsius for three hours, and 22.9 g of solids were obtained by suction filtration. Yield 93.46%.

[0026] Take (10g, 50mmol) solid 2-amino-5-chloronicotinic acid ethyl ester and put it in a 250ml one-necked flask, add 100mL N,N-dimethylformamide dimethyl acetal, and react with 80℃ for 8 hours , the reaction is completed to obtain N,N-dimethyl-N'-2-(3-ethyl carboxylate-5-chloro-pyridinyl)-formamidine intermediate, and the excess N,N-dimethyl Formamide dimethyl acetal, add forty percent chloroacetaldehyde aqueous solution (13.74g, chloroacetaldehyde 70mmol) and 20ml water. React at 100°C for 3 hours. After the reaction is complete, cool to room temperature and add an appropriate amount of saturated sodium carbonate solution to adj...

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Abstract

The invention relates to a synthetic method of ethyl 3-aldehyde-6-chloroimidazo[1,2-a]pyridine-8-formate. The method comprises the following steps: carrying out a substitution reaction on ethyl 2-aminonicotinate and N-chlorosuccinimide in a certain solvent at normal temperature to prepare ethyl 2-amino-5-chloronicotinate; and reacting2-amino-5-chloronicotinate with N,N-dimethylformamide dimethyl acetal to prepare an intermediate, reacting the intermediate with chloroacetaldehyde in a certain solvent at 0-100DEG C without purifying the intermediate, cooling, and drying to obtain ethyl 3-aldehyde-6-chloroimidazo[1,2-a]pyridine-8-formate. The method has the advantages of easily available reaction raw materials, reasonable price, mild reaction conditions, easy operation, easy control and simple post-treatment, and the above obtained product has the advantages of stable quality and high purity.

Description

(1) Technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for synthesizing ethyl 3-formyl-6-chloroimidazo[1,2-a]pyridine-8-carboxylate. (2) Background technology [0002] Ethyl 3-formyl-6-chloroimidazo[1,2-a]pyridine-8-carboxylate is an important intermediate in organic synthesis, mainly used in pharmaceutical intermediates, organic synthesis, organic solvents, and can also be used in dyes Production, pesticide production and spices, etc. This product is a novel pharmaceutical intermediate with great medical value, but its synthesis is difficult, the market price is expensive, and there is a lack of literature and related patent reports. (3) Contents of the invention [0003] The problem to be solved in the present invention is to provide a 3-formyl-6-chloroimidazo[1,2-a]pyridine-8 with simple and reasonable process, low cost, high product purity and suitable for industrialization. - Synthetic method of ...

Claims

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Application Information

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IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 崔淑芬耿宣平来新胜韩猛曹惊涛
Owner SHANDONG YOUBANG BIOCHEM TECH
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