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Method for synthesizing 5-iodo-4-methoxy-2-aminopyridine

A technology of methoxypyridine and aminopyridine is applied in the synthesis field of 5-iodo-4-methoxy-2-aminopyridine, and can solve the problem that there is no public report on the synthesis method of N-iodosuccinimide, Expensive reagents, high reaction temperature, etc., to achieve the effects of low cost, short reaction time and simple synthesis route

Inactive Publication Date: 2017-08-04
KANGHUA SHANGHAI DRUG RES DEV CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this method requires a microwave reaction device, and there are disadvantages such as high reaction temperature, long reaction time, relatively expensive reagents and a large amount of reagents required.
[0003] So far, there is no public report about the synthetic method utilizing N-iodosuccinimide as iodination reagent

Method used

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  • Method for synthesizing 5-iodo-4-methoxy-2-aminopyridine

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Add 2-amino-4-methoxypyridine (7.8g, 62.9mmol) and N,N-dimethylformamide (150mL) into a three-necked flask; add N-iodosuccinimide ( 14.1 g, 62.7 mmol). The reaction solution was stirred at 25°C for 60 minutes. The reaction solution was diluted with water (400mL), filtered to obtain a solid crude product, and separated by silica gel column chromatography (dichloromethane:methanol=20:1) to obtain a brown solid, the target product 5-iodo-4-methoxy-2- Aminopyridine (7.24 g, 28.9 mmol, 46%). The NMR results are as follows: 1 H NMR (400MHz, CDCl 3 ):8.16(s,1H),5.98(s,1H),4.44(br,2H),3.86(s,3H)ppm. Liquid chromatography-mass spectrometry detection results are as follows: LC-MS(ESI):m / z 250.90[M+H] + .

Embodiment 2

[0019] Step 1: The reaction time of 2-amino-4-methoxypyridine and N-iodosuccinimide in N,N-dimethylformamide is 30 minutes, the reaction temperature is 50°C, and the reaction solution is water ( 400mL), filtered to obtain the solid crude product, separated by silica gel column chromatography (dichloromethane:methanol=20:1), to obtain a brown solid, the target product 5-iodo-4-methoxy-2-aminopyridine (yield rate 45.2%). The NMR results are as follows: 1 H NMR (400MHz, CDCl 3 ):8.16(s,1H),5.98(s,1H),4.44(br,2H),3.86(s,3H)ppm. Liquid chromatography-mass spectrometry detection results are as follows: LC-MS(ESI):m / z250.90[M+H] + .

Embodiment 3

[0021] Step 1: The reaction time of 2-amino-4-methoxypyridine and N-iodosuccinimide in N,N-dimethylformamide is 90 minutes, the reaction temperature is 0°C, and the reaction solution is water ( 400mL), filtered to obtain the solid crude product, separated by silica gel column chromatography (dichloromethane:methanol=20:1), to obtain a brown solid, the target product 5-iodo-4-methoxy-2-aminopyridine (yield rate 45.5%). The NMR results are as follows: 1 H NMR (400MHz, CDCl 3 ):8.16(s,1H),5.98(s,1H),4.44(br,2H),3.86(s,3H)ppm. Liquid chromatography-mass spectrometry detection results are as follows: LC-MS(ESI):m / z250.90[M+H] + .

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Abstract

The invention provides a method for synthesizing 5-iodo-4-methoxy-2-aminopyridine. The method comprises the following steps: carrying out a reaction on 2-amino-4-methoxypyridine used as an initial material by using N-iodosuccinimide as an iodization reagent, and carrying out post-treatment and purification after the reaction is finished in order to obtain the 5-iodo-4-methoxy-2-aminopyridine. Compared with the prior art, the method provided by the invention has the advantages of mild reaction conditions, simple synthesis route, short reaction time and low cost.

Description

technical field [0001] The invention relates to a method for synthesizing 5-iodo-4-methoxy-2-aminopyridine. Background technique [0002] 5-iodo-4-methoxy-2-aminopyridine is widely used as a pharmaceutical intermediate. In 2013, PhillipP.Sharp et al. reported for the first time in the journal Organic Letters a synthetic method using 2-amino-4-methoxypyridine as a raw material, reacting with iodine and silver trifluoromethanesulfonate, and using microwave technology. However, this method requires a microwave reaction device, and has disadvantages such as high reaction temperature, long reaction time, relatively expensive reagents, and a large amount of reagents. [0003] So far, there is no public report about the synthesis method using N-iodosuccinimide as iodination reagent. Contents of the invention [0004] The purpose of this invention is to provide a kind of synthetic method of 5-iodo-4-methoxy-2-aminopyridine, to simplify its synthetic process, and reduce productio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/73
CPCC07D213/73
Inventor 徐红岩马敬祥
Owner KANGHUA SHANGHAI DRUG RES DEV CO LTD
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