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Preparation method of 5-aminomethyl pyridine derivative

A technology of aminomethylpyridine and hydroxymethylpyridine, which is applied in the field of preparation of 5-aminomethylpyridine derivatives, can solve the problems of low yield and achieve the effects of high yield, mild conditions and simple process

Inactive Publication Date: 2014-01-08
RENNOTECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

For example, the patent US2006287522A1 discloses that a 5-hydroxymethyl-3-bromopyridine is used as a raw material, and 5-aminomethyl-3-bromopyridine is prepared in two steps of halogen substitution and amination. However, the yield of the method is low, only 36%

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  • Preparation method of 5-aminomethyl pyridine derivative
  • Preparation method of 5-aminomethyl pyridine derivative
  • Preparation method of 5-aminomethyl pyridine derivative

Examples

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Embodiment 15

[0019] The preparation of embodiment 15-aminomethyl-3-bromopyridine

[0020] The preparation of 5-aminomethyl-3-bromopyridine adopts the following process:

[0021] (1) Preparation of 5-azidomethyl-3-bromopyridine: Add 1.00g of 5-hydroxymethyl-3-bromopyridine, 2.63g of diphenylphosphoryl azide and 10mL of tetrahydrofuran into a three-neck flask; nitrogen protection , the reaction system was cooled to below 10°C, and 0.89g of 1,8-diazabicyclo[5.4.0]undec-7-ene was added dropwise to the reaction liquid, and reacted at room temperature for 12h. The volatiles were removed by concentration under reduced pressure, and 0.98 g of 5-azidomethyl-3-bromopyridine was obtained by column chromatography.

[0022] (2) Preparation of 5-aminomethyl-3-bromopyridine: Dissolve 0.98g of 5-azidomethyl-3-bromopyridine in 20ml of THF and 2ml of water, add 2.41g of triphenylphosphine under ice-water bath, 5 The reaction was carried out at ℃ for 16 h; extracted with ethyl acetate, concentrated, and 0....

Embodiment 25

[0027] The preparation of embodiment 25-aminomethyl-3-bromopyridine

[0028] The preparation of 5-aminomethyl-3-bromopyridine adopts the following process:

[0029] (1) Preparation of 5-azidomethyl-3-bromopyridine: Add 0.1mol 5-hydroxymethyl-3-bromopyridine, 0.1mol diphenylphosphoryl azido and 50mL toluene into a three-neck flask; nitrogen protection , the reaction system was cooled to below 10°C, 0.01mol tetrabutylammonium bromide was added dropwise to the reaction solution, and the reaction was refluxed for 8h. Concentrate under reduced pressure to remove volatiles, and obtain 5-azidomethyl-3-bromopyridine by column chromatography.

[0030] (2) Preparation of 5-aminomethyl-3-bromopyridine: Dissolve 0.05mol of 5-azidomethyl-3-bromopyridine in 20ml of methanol and 2ml of water, add 5mmol of palladium carbon in an ice-water bath, and place at -5°C Reaction for 30h; extraction with ethyl acetate, concentration, and column chromatography to obtain the product.

Embodiment 35

[0031] The preparation of embodiment 35-aminomethyl-3-bromopyridine

[0032] The preparation of 5-aminomethyl-3-bromopyridine adopts the following process:

[0033] (1) Preparation of 5-azidomethyl-3-bromopyridine: Add 0.1mol 5-hydroxymethyl-3-bromopyridine, 0.3mol diphenylphosphoryl azido and 50mL N,N- Dimethylformamide; under nitrogen protection, cool the reaction system below 10°C, add 0.1mol tetrabutylammonium iodide, 0.1mol N,N-diisopropylethylamine, 0.05mol p-toluenesulfonyl chloride , 0.05mol2,4,6-trimethylbenzenesulfonyl chloride was added dropwise to the reaction solution, and reacted at room temperature for 16h. Concentrate under reduced pressure to remove volatiles, and obtain 5-azidomethyl-3-bromopyridine by column chromatography.

[0034] (2) Preparation of 5-aminomethyl-3-bromopyridine: Dissolve 0.05mol 5-azidomethyl-3-bromopyridine in 20ml of N,N-dimethylformamide and 2ml of water, and add 5mmol of aluminum chloride was reacted at room temperature for 8h; ext...

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Abstract

The invention provides a preparation method of a 5-aminomethyl pyridine derivative, which comprises the following steps: performing a reaction on 3-substituted 5-hydroxymethylpyridine, an azide reagent and a catalyst to obtain 3-substituted 5-azido methylpyridine; and performing a reaction on the 3-substituted 5-azido methylpyridine and a reducing agent to obtain the 5-aminomethyl pyridine derivative. The preparation method has the advantages of simple process, mild conditions, safety in operation and high yield.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a preparation method of 5-aminomethylpyridine derivatives. Background technique [0002] 5-aminomethylpyridine derivatives are a class of important pharmaceutical intermediates, such as methyl 5-aminomethylnicotinate and 5-aminomethyl-3-bromopyridine can be used to prepare a variety of important raw materials. 5-Aminomethylpyridine derivatives are usually prepared by converting the hydroxyl groups in 5-hydroxymethylpyridine derivatives into functional groups. For example, the patent US2006287522A1 discloses that a 5-hydroxymethyl-3-bromopyridine is used as a raw material, and 5-aminomethyl-3-bromopyridine is prepared in two steps of halogen substitution and amination. However, the yield of the method is Low, only 36%. Contents of the invention [0003] Purpose of the invention: The purpose of the present invention is to provide a method for preparing 5-aminomethylpyridine de...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/61C07D213/80C07D213/803
CPCC07D213/61C07D213/80C07D213/803
Inventor 邹正才康柳
Owner RENNOTECH
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