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Synthesis method for 3-aldehyde imidazo-[1, 2-alpha] pyridine-8-ethyl formate

A kind of technology of ethyl formate and aldehyde imidazole is applied in the synthesis field of 3-aldehyde imidazo[1,2-a]pyridine-8-ethyl carboxylate, which can solve synthesis difficulties, lack of literature and patent reports, and market price Expensive and other problems, to achieve the effect of simple post-processing, stable product quality and easy operation

Inactive Publication Date: 2015-09-02
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

[0018] Put 100mmol (16.6g) of 2-aminonicotinic acid ethyl ester solid in a 250ml single-necked flask, add 100mL N,N-dimethylformamide dimethyl acetal, and react at 60°C for 5 hours. After the reaction is completed, N, N-Dimethyl-N'-2-(3-ethylpyridinylcarboxylate)-formamidine intermediate, rotary evaporation to remove excess N,N-dimethylformamide dimethyl acetal, add percent Forty chloroacetaldehyde aqueous solution (12.76g, chloroacetaldehyde 65mmol), react at 0°C for 10 hours, after the reaction is completed, cool to room temperature, add an appropriate amount of saturated sodium bicarbonate solution, and adjust the pH to about 8. Stand still for three hours, the solid precipitates, dissolve all the solids in 200ml ethyl acetate, wash with water three times, each time with 100ml, the purpose is to remove excess chloroacetaldehyde, then wash twice with saturated saline, each time 100ml , and then dried with anhydrous sodium sulfate, concentrated by rotary evaporation, and drie...

Embodiment 2

[0020] Put 100mmol (16.6g) of 2-aminonicotinic acid ethyl ester solid in a 250ml single-necked flask, add 100mL of N,N-dimethylformamide dimethyl acetal, and react at 100°C for 5 hours. After the reaction is completed, N, N-Dimethyl-N'-2-(3-ethylpyridinylcarboxylate)-formamidine intermediate, rotary evaporation to remove excess N,N-dimethylformamide dimethyl acetal, add percent Forty chloroacetaldehyde aqueous solution (14.72g, chloroacetaldehyde 75mmol), reacted at 60°C for 15 hours, after the reaction was completed, cooled to room temperature, added an appropriate amount of sodium hydroxide solution, and adjusted the pH to about 8. Stand for three hours, the solid precipitates, the solid is dissolved in 200ml of ethyl acetate, washed three times with water, each time with 100ml, the purpose is to remove excess chloroacetaldehyde, then washed twice with saturated saline, each time 100ml, and then After drying with anhydrous sodium sulfate, concentrating by rotary evaporation,...

Embodiment 3

[0022] Put 100mmol (16.6g) of 2-aminonicotinic acid ethyl ester solid in a 250ml single-necked flask, add 100mL N,N-dimethylformamide dimethyl acetal, and react at 80°C for 8 hours, and the reaction is completed to obtain N ,N-Dimethyl-N'-2-(3-ethylpyridinylcarboxylate)yl-formamidine intermediate, rotary evaporation to remove excess N,N-dimethylformamide dimethyl acetal, add % Forty 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 adjust the pH to about 8. Stand for three hours, the solid precipitates, the solid is dissolved in 200ml of ethyl acetate, washed three times with water, each time with 100ml, the purpose is to remove excess chloroacetaldehyde, then washed twice with saturated saline, each time 100ml, and then After drying with anhydrous sodium sulfate, concentrating by rot...

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Abstract

The present invention belongs to the field of organic synthesis, and particularly relates to a synthesis method for 3-aldehyde imidazo-[1, 2-alpha] pyridine-8-ethyl formate, which comprises the following steps of obtaining a purification-free intermediate through the dimethyl acetal reaction between 2-amino-nicotinic acid ethyl ester and N, N-dimethyl formamide; reacting the intermediate with chloroacetaldehyde at 0-100 DEG C in a certain solvent, cooling the solvent after the reaction, adding alkali of a certain amount in the solvent to precipitate solids, and finally obtain 3-aldehyde imidazo-[1, 2-alpha] pyridine-8-ethyl formate after the dissolving, drying and rotary evaporation process. The raw materials of the method are readily available, reasonable in cost, mild in reaction conditio, easy to operate and control, and simple in post-processing. Products obtained through the method are stable in quality and high in purity.

Description

(1) Technical field [0001] The invention belongs to the field of organic synthesis, in particular to a method for synthesizing ethyl 3-formyl imidazo[1,2-a]pyridine-8-carboxylate. (2) Background technology [0002] Ethyl 3-formylimidazo[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 dye production and 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 simple and reasonable process, low cost, high product purity, and industrialized ethyl 3-formyl imidazo[1,2-a]pyridine-8-carboxylate for the prior art synthetic method. [0004] The present inv...

Claims

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Application Information

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IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 崔淑芬韩猛来新胜曹惊涛
Owner SHANDONG YOUBANG BIOCHEM TECH
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