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Novel synthetic method for 2-amino-4-bromopyridine

A synthetic method, bromopyridine technology, applied in the direction of organic chemistry, can solve the problems of high raw material cost, low yield, poor repeatability, etc., and achieve the effect of strong repeatability, high yield, and low cost

Inactive Publication Date: 2014-05-07
CHENGDU KAIXIN TIANRUI TECH DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The cost of raw materials is very high in this method. When using dppa for rearrangement, the yield is very low and the repeatability is very poor. It cannot be enlarged to industrialization at all.

Method used

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  • Novel synthetic method for 2-amino-4-bromopyridine
  • Novel synthetic method for 2-amino-4-bromopyridine
  • Novel synthetic method for 2-amino-4-bromopyridine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment 1 adopts the inventive method to produce

[0025] 0.5kg of 2-amino 4-methylpyridine, the amino group is acetylated (1 part of 2-amino-4-picoline: 1.2 parts of acetylating agent, the acetylating agent is ethyl acetoacetate), and then oxidized to obtain 2-acetylamino - 0.6kg of pyridine 4-formic acid. Then, 0.4 kg of 4-amino boc-2-acetylaminopyridine was obtained by dppa rearrangement, and 0.4 kg of 2-amino-4-bromopyridine was directly obtained by reflux of hydrobromic acid. The yield was 50%, and the purity was 98%. For details, see figure 1 .

Embodiment 2

[0026] Embodiment 2 adopts the inventive method to produce

[0027] 5kg of 2-amino 4-methylpyridine, the amino group is acetylated (1 part of 2-amino-4-picoline: 1.2 parts of acetylating agent, the acetylating agent is ethyl acetoacetate), and then oxidized to obtain 2-acetylamino- 4-pyridine carboxylic acid 6.05kg. Then, 4 kg of 4-amino boc-2-acetylaminopyridine was obtained by dppa rearrangement, and 4 kg of 2-amino-4-bromopyridine was directly obtained by reflux of hydrobromic acid. The yield was 50%, and the purity was 98%.

Embodiment 3

[0028] Embodiment 3 adopts the inventive method to produce

[0029] 10kg of 2-amino 4-methylpyridine, the amino group is acetylated (1 part of 2-amino-4-picoline: 1.2 parts of acetylating agent, the acetylating agent is ethyl acetoacetate), and then oxidized to obtain 2-acetylamino- 4-pyridine carboxylic acid 12.1kg. Then, 8.2 kg of 4-amino boc-2-acetylaminopyridine was obtained by dppa rearrangement, and 8.1 kg of 2-amino-4-bromopyridine was directly obtained by reflux of hydrobromic acid. The yield was 51.2%, and the purity was 98.3%.

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Abstract

The invention relates to synthesis of 2-amino-4-bromopyridine, which belongs to the field of organic synthesis. The invention provides an advanced and novel synthetic method for 2-amino-4-bromopyridine, and the method has the advantages of low cost for raw materials and high yield. According to the invention, cheap 2-amino-4-methylpyridine is used as a raw material, an amino group is subjected to acetyl protection at first, and then oxidation is carried out so as to obtain 2-acetylamino-4-pyridinecarboxylic acid; and then dppa rearrangement is carried out so as to obtain 4-amino-boc-2-acetylamino-pyridine, and hydrobromic acid reflux is carried out so as to directly obtain 2-amino-4-bromopyridine. The method has yield of more than 98%.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to the synthesis of 2-amino-4-bromopyridine. Background technique [0002] 2-amino-4-bromopyridine, also known as 4-bromo-2-aminopyridine, English name 2-amino-4-bromopyridine. Molecular formula: , molecular weight: 173.9987. InChI: InChI=1 / C4H4BrN3 / c5-3-1-2-7-4(6)8-3 / h1-2H, (H2, 6, 7, 8). Density 1.844g / cm 3 , boiling point 340.7°C at 760mmHg, flash point 159.9°C, CAS number: 84249-14-9; 343926-69-2. [0003] Since the bromine atom / amino group in the molecule can continue to biochemically introduce other functional groups, many novel and diverse heterocyclic compounds can be designed and synthesized. Therefore, 2-amino-4-bromopyridine is a widely used pharmaceutical intermediate. [0004] In the prior art, 4-bromopyridine 2-methyl is usually oxidized to 4-bromopyridine-2-formate, then rearranged with dppa to obtain 2-boc amino-4-bromopyridine, and finally deboc to obtain 2-amin...

Claims

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Application Information

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IPC IPC(8): C07D213/73
CPCC07D213/73
Inventor 寿越晗
Owner CHENGDU KAIXIN TIANRUI TECH DEV
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