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

A technology of ethyl formate and a synthetic method, applied in directions such as organic chemistry, can solve the problems of lack of literature and patent reports, high market price, difficult synthesis, etc., and achieve the effects of stable product quality, easy operation, and simple post-processing

Active Publication Date: 2015-03-11
陕西友帮生物医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This technology makes it easier for people who want something that's expensive or difficult to make at home compared with trying out new things from outside sources like restaurants or grocery stores. It also has several technical benefits such as being able to react quickly without getting too much pressure on them while still producing good products consistently over time.

Problems solved by technology

The technical problem addressed by this patented method for producing ethylenediaminetriamidiolium salt (Et3) involves finding ways to make it easier than current methods that require high prices or limited supplies from other sources such as bacteria.

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 (19.58g) of N-bromosuccinimide 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] Put the obtained 2-amino-5-bromonicotinic acid ethyl ester (24.1g, 98.36mmol) solid in a 250ml one-necked flask, add 200mL N,N-dimethylformamide dimethyl acetal, and react at 70°C After 5 hours, the N,N-dimethyl-N'-2-(3-ethyl carboxylate-5-bromo-pyridinyl)-formamidine intermediate was obtained at the end of the reaction, and the excess N,N-di Methylformamide dimethyl acetal, add 40% chloroacetaldehyde aqueous solution (25.09g, chloroacetaldehyde 127.86mmol), react at 60°C for 10 hours, after the reaction is completed, cool to r...

Embodiment 2

[0022] 100mmol (16.6g) of ethyl 2-aminonicotinate was reacted with 110mmol (19.58g) of N-bromosuccinimide 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 23.6 g of solids, with a yield of 98.36%. Acetonitrile was recovered by rotary evaporation.

[0023] Put the obtained 2-amino-5-bromonicotinic acid ethyl ester (23.6g, 98.36mmol) solid in a 250ml one-necked flask, add 200mL N,N-dimethylformamide dimethyl acetal, and react at 120°C After 3 hours, the N,N-dimethyl-N'-2-(3-ethyl carboxylate-5-bromo-pyridinyl)-formamidine intermediate was obtained at the end of the reaction, and the excess N,N-di Methylformamide dimethyl acetal, add 40% chloroacetaldehyde aqueous solution (25.09g, chloroacetaldehyde 127.86mmol), react at 100°C for 5 hours, after the reaction is completed, cool to...

Embodiment 3

[0025] 100mmol (16.6g) of ethyl 2-aminonicotinate was reacted with 110mmol (19.58g) of N-bromosuccinimide 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 23.5 g of solids were obtained by suction filtration. Yield 95.9%.

[0026] Put the obtained solid in a 250ml one-necked flask, add 200mL (179.2g) N,N-dimethylformamide dimethyl acetal, and 2-amino-5-bromonicotinic acid ethyl ester (23.5g, 95.9mmol ) at 50°C for 8 hours, and the N,N-dimethyl-N'-2-(3-formic acid ethyl ester-5-bromo-pyridinyl)-formamidine intermediate was obtained after the reaction was completed, and the excess was removed by rotary evaporation To N,N-dimethylformamide dimethyl acetal, add 40% chloroacetaldehyde aqueous solution (24.47g, chloroacetaldehyde 124.67mmol) and 20ml water. React at 100°C for 10 hours. After the reaction is complete, cool to room temperature and add an approp...

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Abstract

The invention relates to a synthetic method of ethyl 3-aldehyde-6-bromoimidazo[1,2-a]pyridine-8-formate. The method comprises the following steps: carrying out a substitution reaction on ethyl 2-aminonicotinate and N-bromosuccinimide in a certain solvent at normal temperature to prepare ethyl 2-amino-5-bromonicotinate; and reacting2-amino-5-bromonicotinate with N,N-dimethylformamide dimethyl acetal at 30-150DEG C to prepare an intermediate, reacting the intermediate with chloroacetaldehyde in a certain solvent at 60-160DEG C without purifying the intermediate, cooling, and drying to obtain ethyl 3-aldehyde-6-bromoimidazo[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

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Claims

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Application Information

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Owner 陕西友帮生物医药科技有限公司
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