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3-iodine-5-methoxypyridine synthesis method

A technology of methoxypyridine and synthesis method, which is applied in the field of synthesis of 3-iodo-5-methoxypyridine, and achieves the effect of simple reaction conditions and easy separation

Inactive Publication Date: 2017-11-03
KANGHUA SHANGHAI DRUG RES DEV CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The purpose of this invention is to provide a kind of synthetic method of 3-iodo-5-methoxypyridine, mainly solve the technical problem of simplifying its synthetic method

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0010] step 1:

[0011] Add 3-amino-5-methoxypyridine (10.0 g, 80.6 mmol) and 1.6 M sulfuric acid solution (200 mL) into the three-necked flask; add sodium nitrite (6.0 g, 88.6 mmol) at -5°C. The reaction solution was stirred at -5°C for 10 minutes. Add potassium iodide (40.0 g, 242 mmol) aqueous solution (100 mL) at -5°C and stir at -5°C for 15 minutes. The reaction solution was basified with 2 M sodium hydroxide solution until the pH was equal to 8-9, water (100 mL) was added, extracted with ethyl acetate (100 mL x 3); the organic phases were combined, and saturated sodium bisulfite solution (100 mL) and saturated brine (100 mL), dried over sodium sulfate, and filtered. The filtrate was spin-dried, and the crude product was separated by silica gel column chromatography (petroleum ether: ethyl acetate volume ratio = 40:1) to obtain a white solid, the target compound 1 (10.2 g, 43.4 mmol, 48 %). 1 H NMR (300 MHz, D 2 O) 8.38 (d, J = 2.7 Hz, 1H), 8.28(d, J = 2.7 Hz, 1H), 7....

Embodiment 2

[0012] Example 2, step 1: the reaction time of 3-amino-5-methoxypyridine and sodium nitrite in 1.6 M sulfuric acid solution is 5 minutes, and the reaction temperature is 0 ° C; the reaction time of diazonium salt and potassium iodide is 10 minutes, Reaction temperature is 0 ℃, all the other are with embodiment 1.

Embodiment 3

[0013] Example 3, Step 1: The reaction time of 3-amino-5-methoxypyridine and sodium nitrite in 1.6 M sulfuric acid solution is 15 minutes, and the reaction temperature is -10°C; the reaction time of diazonium salt and potassium iodide is 20 minutes , the reaction temperature is-10°C, and the rest are the same as in Example 1.

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PUM

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Abstract

The invention relates to a 3-iodine-5-methoxypyridine synthesis method, and mainly aims to solve the technical problem of simplification of the 3-iodine-5-methoxypyridine synthesis method. The 3-iodine-5-methoxypyridine synthesis method is characterized by including the step: adding sodium nitrite into ice-salt baths of 3-amino-5-methoxypyridine and sulfuric acid solution to react to generate diazonium salt; adding iodide, replacing diazonium of the diazonium salt with iodine negative ions, taking strong alkaline solution as reaction liquid, adjusting pH (potential of hydrogen) to be 8-9, performing ethyl acetate extraction, performing spin drying, purifying coarse products by a chromatographic column to obtain a target product 1, namely, the 3-iodine-5-methoxypyridine. The 3-iodine-5-methoxypyridine mainly serves as a medical intermediate.

Description

technical field [0001] The present invention relates to the synthesis of 3-iodo-5-methoxypyridine (CAS: 873302-36-4). Background technique [0002] 3-iodo-5-methoxypyridine is widely used as a pharmaceutical intermediate. In 2015, Mao Chen et al. reported for the first time in the Journal of Applied Chemistry a synthetic method using 3-bromo-5-methoxypyridine as a raw material and cuprous iodide as a catalyst using Continuous-Flow technology. But so far, there is no public report about its synthesis method through diazotization reaction. Contents of the invention [0003] The purpose of the present invention is to provide a synthetic method of 3-iodo-5-methoxypyridine, which mainly solves the technical problem of simplifying the synthetic method. [0004] The technical scheme of the present invention is: a kind of synthetic method of 3-iodo-5-methoxypyridine, it is characterized in that comprising the following steps: 3-amino-5-methoxypyridine, adding nitrous acid under ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/65
CPCC07D213/65
Inventor 徐红岩马敬祥
Owner KANGHUA SHANGHAI DRUG RES DEV CO LTD