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Preparation method of 2-(5-bromo-3-methylpyridine-2-yl) acetic acid hydrochloride

A technology of acetic acid hydrochloride and picoline, applied in the direction of organic chemistry, etc., to achieve the effects of improving yield and purity, simple operation, and high product yield

Pending Publication Date: 2020-12-11
埃法姆药物研发(宁夏)有限公司
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Problems solved by technology

[0003] 2-(5-Bromo-3-methylpyridin-2-yl)acetic acid hydrochloride is a kind of pyridine acetic acid derivatives, currently 2-(5-bromo-3-methylpyridin-2-yl)ethyl The synthesis method of hydrochloride is rarely reported in the literature

Method used

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  • Preparation method of 2-(5-bromo-3-methylpyridine-2-yl) acetic acid hydrochloride
  • Preparation method of 2-(5-bromo-3-methylpyridine-2-yl) acetic acid hydrochloride
  • Preparation method of 2-(5-bromo-3-methylpyridine-2-yl) acetic acid hydrochloride

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preparation example Construction

[0019] A preparation method of 2-(5-bromo-3-methylpyridin-2-yl)acetic acid hydrochloride, the preparation method comprising the steps of:

[0020] (1) According to the volume ratio of n-butyllithium (2.5M), tetrahydrofuran and compound A in tetrahydrofuran solution is 16~18:100:35, the solid-liquid g / mL ratio of acetonitrile and compound A in tetrahydrofuran solution is 1:19 , take the raw material, put tetrahydrofuran into the reactor, protect it with nitrogen, add n-butyllithium (2.5M), cool down to -80~-75℃, add acetonitrile dropwise, keep warm for 1~2h, add tetrahydrofuran of compound A Solution, keep stirring for 2 hours, heat up to 30-35°C, and stir for 1 hour to obtain compound B;

[0021] (2) According to the solid-to-liquid g / mL ratio of compound B and concentrated hydrochloric acid (12M) as 1:4.5, take raw materials, mix compound B and concentrated hydrochloric acid (12M), raise the temperature to 80-85°C, and stir for 1-2 hours , to obtain compound C, which is 2-(5...

Embodiment 1

[0023] Preparation of Compound B:

[0024]

[0025] Put 1000mL tetrahydrofuran into the reactor, under nitrogen protection, add 160mL n-butyllithium (2.5M), cool down to -80°C, add 18.4mL acetonitrile dropwise, keep the reaction for 1h, add 350mL tetrahydrofuran solution containing 50g compound A, keep warm Stir for 2 hours, raise the temperature to 30°C, stir for 1 hour, add saturated aqueous ammonium chloride solution (500mL), extract with EA (500mL*3), combine the organic phases, mix the sample and pass through the column to obtain 35.3g of light yellow oil, and compound B, The yield was 83.9%, and the purity was 98.3%.

[0026] Compound C is the preparation of 2-(5-bromo-3-methylpyridin-2-yl)acetic acid hydrochloride:

[0027]

[0028] (2) Mix 30g of compound B and 135mL of concentrated hydrochloric acid (12M), raise the temperature to 80°C, stir and react for 1h, and detect by TLC. After the reaction of raw materials is completed, the solvent is distilled off under...

Embodiment 2

[0031] Preparation of Compound B:

[0032]

[0033] Put 1000mL tetrahydrofuran into the reactor, under nitrogen protection, add 170mL n-butyllithium (2.5M), cool down to -78°C, add 18.4mL acetonitrile dropwise, keep the reaction for 1.5h, add 350mL tetrahydrofuran solution containing 50g compound A, Keep stirring for 2 hours, raise the temperature to 33°C, stir for 1 hour, add saturated ammonium chloride aqueous solution (500mL), extract with EA (500mL*3), combine the organic phase, mix the sample and pass through the column to obtain 36.2 light yellow oil, and compound B, The yield was 86.0%, and the purity was 99.3%.

[0034] Compound C is the preparation of 2-(5-bromo-3-methylpyridin-2-yl)acetic acid hydrochloride:

[0035]

[0036] (2) Mix 30g of compound B and 135mL of concentrated hydrochloric acid (12M), raise the temperature to 83°C, stir and react for 1.5h, and detect by TLC. After the reaction of the raw materials is completed, the solvent is distilled off und...

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Abstract

The invention belongs to the technical field of medical intermediates, and particularly relates to a preparation method of 2-(5-bromine- 3-methylpyridine-2-yl) acetic acid hydrochloride. According tothe preparation method, n-butyllithium and acetonitrile are subjected to a reaction so as to increase protection of bromine in a compound A, and then the compound A is added for a reaction so as to form a compound B so that the yield and the purity of the product are improved, side reactions are avoided, and the compound B and concentrated hydrochloric acid are subjected to a reaction, and the 2-(5-bromine-3-methyl pyridine-2-yl) acetic acid hydrochloride with high purity and high yield is obtained; the synthetic route of the 2-(5-bromine-3-methyl pyridine-2-yl) acetic acid hydrochloride is short, the design is reasonable, the operation is simple, the control is easy, and the product yield is higher.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical intermediates, and specifically relates to a preparation method of 2-(5-bromo-3-methylpyridin-2-yl)acetic acid hydrochloride. Background technique [0002] Pyridine acetic acid derivatives have attracted more and more attention from researchers in the chemical field in recent years because they contain active carboxylic acid functional groups, which can be combined with active hydroxyl and other functional groups to derive many active compounds. [0003] 2-(5-Bromo-3-methylpyridin-2-yl)acetic acid hydrochloride is a kind of pyridine acetic acid derivatives, currently 2-(5-bromo-3-methylpyridin-2-yl)ethyl The synthesis method of hydrochloride is rarely reported in the literature. 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. Co...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/61
CPCC07D213/61
Inventor 史建云刘超
Owner 埃法姆药物研发(宁夏)有限公司
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