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Preparation method of 2-amino-5-bromopyridine

A technology of aminopyridine and bromopyridine, which is applied in the field of preparation of 2-amino-5-pyridine, can solve the problems of many 3-position by-products, expensive brominating agent, corrosiveness, etc., and achieve low cost and mild reaction conditions , the effect of reducing waste

Inactive Publication Date: 2020-04-24
常州传侑环保科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to overcome technical deficiencies such as expensive bromination agent in the prior art, corrosivity, and many by-products at the 3-position, and provide a new preparation method of 2-amino-5-bromopyridine

Method used

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  • Preparation method of 2-amino-5-bromopyridine

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Add 9.4g of 2-aminopyridine (0.1mol), 37.6g of phenyltrimethylammonium tribromide (0.1mol) and 300ml of chloroform into a 1L three-necked flask, insert a mechanical stirrer, a thermometer and a condensing reflux tube into the three-necked flask , start stirring to make it evenly mixed, stir at 30°C for 2 hours, wash with 40ml of saturated sodium chloride solution prepared in advance, the water phase is in the upper layer, and the organic phase is in the lower layer. Wash with water 2-3 times, separate the layers, dry with anhydrous sodium sulfate, filter, and remove the solvent chloroform by rotary evaporation of the organic phase to obtain an oil, cool with ice water, add water to precipitate a solid, and obtain a crude product, recrystallize with benzene, filter, After drying, 10 g of yellow solid was obtained with a yield of 81%.

Embodiment 2

[0020] Add 9.4g of 2-aminopyridine (0.1mol), 37.6g of phenyltrimethylammonium tribromide (0.1mol) and 300ml of chloroform into a 1L three-necked flask, insert a mechanical stirrer, a thermometer and a condensing reflux tube into the three-necked flask , start stirring to make it evenly mixed, stir at 25°C for 2 hours, wash with 40ml of saturated sodium chloride solution prepared in advance, the water phase is in the upper layer, and the organic phase is in the lower layer. Wash with water 2-3 times, separate the layers, dry with anhydrous sodium sulfate, filter, and remove the solvent chloroform by rotary evaporation of the organic phase to obtain an oil, cool with ice water, add water to precipitate a solid, and obtain a crude product, recrystallize with benzene, filter, After drying, 8.43 g of yellow solid was obtained, with a yield of 78%.

[0021] This embodiment is the best implementation mode.

Embodiment 3

[0023] Add 9.4g of 2-aminopyridine (0.1mol), 37.6g (0.1mol of phenyltrimethylammonium tribromide) and 300ml of dichloromethane into a 1L three-necked flask, insert a mechanical stirrer, a thermometer and a condenser in the three-necked flask Return the tube, start stirring to make it evenly mixed, stir at 30°C for 2 hours, wash with 40ml of saturated sodium chloride solution prepared in advance, the water phase is in the upper layer, and the organic phase is in the lower layer. Wash with 20ml of water for 2-3 times, separate layers, dry with anhydrous sodium sulfate, filter, and remove the solvent chloroform by rotary evaporation of the organic phase to obtain an oil, cool with ice water, add water to precipitate a solid, obtain a crude product, recrystallize with benzene, After filtering and drying, 8.1 g of yellow solid was obtained, with a yield of 75%.

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Abstract

The invention belongs to the technical field of organic synthesis, and specifically relates to a preparation method of 2-amino-5-bromopyridine. The method comprises the following steps: 2-aminopyridine serves as a raw material, dichloromethane or trichloromethane serves as a solvent, 2-aminopyridine and phenyl trimethyl ammonium tribromide carry out reactions for 1-3 hours at the temperature of 20-50 DEG C, and the molar ratio of 2-aminopyridine to phenyl trimethyl ammonium tribromide is 0.7-1.4. The preparation method provided by the invention has the beneficial effects that (1) the generation of a large number of 3-position byproducts in a traditional preparation method is avoided, and the waste of raw materials and the load of subsequent separation are reduced; and (2) the raw materialnamely 2-aminopyridine is easy to obtain and low in cost, the synthesis route has the advantages of high yield and mild conditions, no 3-position byproduct is generated in the whole process, and the preparation method has an industrialization prospect.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of 2-amino-5-pyridine. Background technique [0002] Pyridine and its derivatives are widely distributed in nature. Many plant components such as alkaloids contain pyridine ring compounds in their structures, which are the basis for the production of many important compounds, such as medicines, pesticides, dyes, surfactants, rubber additives, feed additives, food additives, adhesives, etc. Indispensable raw material in production. 2-Amino-5-bromopyridine is an important pharmaceutical intermediate that can be used to synthesize PI 3 Kinase inhibitors, halopyridine derivatives and thiazolylthiourea compounds, aminopyridine derivatives selective dopamine D 3 Receptor agonists, synthetic imidazo[1,2-a]pyridine compounds VEGFR-2 inhibitors and other drugs, also used in the treatment of autoimmune diseases, inflammatory diseases, cardiovas...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/73
CPCC07D213/73
Inventor 倪俊
Owner 常州传侑环保科技有限公司
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