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A kind of synthetic method of 2-amino-3-bromoisonicotinic acid methyl ester

A kind of technology of methyl isonicotinate and synthesis method, which is applied in the synthesis field of 2-amino-3-bromoisonicotinic acid methyl ester and achieves the effects of good purity and high yield

Active Publication Date: 2022-05-10
阿里生物新材料(常州)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are few reports in the literature on the synthesis of 2-amino-3-bromoisonicotinic acid methyl ester

Method used

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Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0018] A kind of synthetic method of 2-amino-3-bromoisonicotinic acid methyl ester, this synthetic method comprises the steps:

[0019] (1) The solid-to-liquid ratio g / mL of compound A and tetrahydrofuran is 1:12, the mass ratio of compound A and diisopropylamine is 5:3~5, and the volume ratio of n-butyllithium (2M) to tetrahydrofuran is 1 : 3~6, take material, put diisopropylamine and tetrahydrofuran into the reactor, nitrogen protection, cool to -80~-75 ℃, add n-butyllithium, stir evenly, heat up to 30~35 ℃, with Stir at 600r / min for 1~3h, cool to -80~-75°C, add compound A, stir for 2~4h, then protect with carbon dioxide, raise the temperature to 30~35°C, react for 15~20h to get compound B;

[0020] (2) According to the solid-to-liquid ratio g / mL of compound B and ammonia water as 1:15-20, take the material, add compound B and ammonia water with a mass fraction of 30% into the autoclave, heat to 95-105°C, and react 13 ~17h, the compound C is obtained;

[0021] (3) Accordin...

Embodiment 1

[0023] A kind of synthetic method of 2-amino-3-bromoisonicotinic acid methyl ester, this synthetic method comprises the steps:

[0024] (1) Put 15g of diisopropylamine and 300mL of tetrahydrofuran into the reactor, under nitrogen protection, cool to -80°C, add 100mL of n-butyllithium (2M), stir evenly, raise the temperature to 30°C, and stir at 600r / min for 1h , cooled to -80°C, added 25g of compound A, stirred for 2h, then protected with carbon dioxide, raised the temperature to 30°C, reacted for 15h, TLC detection, the raw material reaction was complete, under ice-water bath, dropwise added saturated potassium carbonate aqueous solution (80mL), added Water 120mL, the water phase was adjusted to pH 3 with 4M hydrochloric acid, stirred for 0.5h, extracted with ethyl acetate (200mL*2), and the organic phase was concentrated to obtain 25.3g of off-white solid, namely Compound B, with a yield of 81%. 97.2% purity;

[0025] (2) Add 20g of compound B and 300mL of ammonia water wit...

Embodiment 2

[0029] A kind of synthetic method of 2-amino-3-bromoisonicotinic acid methyl ester, this synthetic method comprises the steps:

[0030] (1) Put 20g of diisopropylamine and 300mL of tetrahydrofuran into the reactor, under nitrogen protection, cool to -78°C, add 60mL of n-butyl lithium (2M), stir evenly, raise the temperature to 33°C, and stir at 600r / min for 2h , cooled to -78°C, added 25g of compound A, stirred for 3h, then protected with carbon dioxide, heated to 33°C, reacted for 18h, TLC detected that the raw materials were completely reacted, added dropwise saturated potassium carbonate aqueous solution (80mL) in an ice-water bath, added Water 120mL, the water phase was adjusted to pH 3 with 4M hydrochloric acid, stirred for 0.5h, extracted with ethyl acetate (200mL*2), and the organic phase was concentrated to obtain 25.6% off-white solid, that is, compound B with a yield of 84.8%, 98.2% purity;

[0031] (2) Add 20g of compound B and 360mL of ammonia water with a mass fr...

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PUM

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Abstract

The invention belongs to the technical field of pharmaceutical intermediates, in particular to a method for synthesizing 2-amino-3-bromoisonicotinic acid methyl ester. The present invention uses compound A as a starting material, reacts with diisopropylamine, etc. to form compound B, and then through subsequent reactions such as the reaction of compound B, 2-amino-3-bromoisonicotinic acid methyl ester is formed. The present invention The synthetic method of 2-amino-3-bromoisonicotinic acid methyl ester is proposed for the first time; the product obtained by the present invention has higher yield and good purity.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical intermediates, in particular to a method for synthesizing 2-amino-3-bromoisonicotinic acid methyl ester. Background technique [0002] The compound 2-amino-3-bromoisonicotinic acid methyl ester and related derivatives are widely used in medicinal chemistry and organic synthesis. At present, there are few reports on the synthesis methods of 2-amino-3-bromoisonicotinic acid methyl ester. Therefore, it is necessary to develop a synthetic method that is easy to obtain raw materials, easy to operate, easy to control the reaction, suitable for overall yield, and suitable for industrial production. Contents of the invention [0003] Technical problem to be solved by the present invention: Aiming at the above-mentioned problems, a method for synthesizing 2-amino-3-bromoisonicotinic acid methyl ester is provided. [0004] In order to solve the problems of the technologies described above, the pr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/79C07D213/803
CPCC07D213/79C07D213/803
Inventor 许义波戴红升
Owner 阿里生物新材料(常州)有限公司
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