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Preparation and purification method of 5-(2-fluorophenyl)-1-(pyridine-3-ylsulfonyl)-1H-pyrrole-3-formaldehyde

A technology for the preparation of sulfonyl and formaldehyde, which is applied in the field of chemical synthesis and preparation, can solve the problems of complex processing, high production cost, and many reaction by-products, and achieve the effects of easy control of process conditions, low production cost, and simple post-treatment

Inactive Publication Date: 2020-06-05
SHANDONG XINHUA PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore the shortcoming of this method technology is, needs to use a large amount of 15-crown-5 in the reaction, stays in mother liquor and can't reclaim, can only be discarded, causes certain resource waste and environmental pollution; There are many by-products, which require a large amount of saturated brine to wash, solvent ethyl acetate to extract, and finally need to be purified by silica gel column chromatography and mixed solvent crystallization to obtain the target compound, resulting in low product yield, low production efficiency, and high energy consumption. There are many wastes, high production cost, and it is difficult to realize industrial production

Method used

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  • Preparation and purification method of 5-(2-fluorophenyl)-1-(pyridine-3-ylsulfonyl)-1H-pyrrole-3-formaldehyde

Examples

Experimental program
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Effect test

Embodiment 1

[0018] A. In a 10L glass-lined reactor equipped with a stirrer, a thermometer, a vacuum pressure gauge, etc., add 4725g of acetonitrile and 189g of compound (Ⅲ) under stirring, cool down to 15°C, add 140g of potassium hydroxide powder, and replace the air with nitrogen Afterwards, heat preservation and stirring reaction for 1.5 hours. Then, 397.7 g of pyridine-3-sulfonyl chloride was added dropwise to the reaction liquid, the reaction temperature was controlled at 30±2° C., and the reaction was carried out while insulated and stirred for 1 hour. Hydraulically filter the reaction mixture into the still, and recover the solvent by distillation under reduced pressure until there is no distillate. The internal temperature is controlled below 50°C, and the vacuum degree is ≥-0.07MPa. After the concentration is completed, add 472.5g ethyl acetate and 2362.5g n-hexane Add 13 g of activated carbon under stirring, heat up to 70°C for decolorization for 0.5 hours, press filter, cool dow...

Embodiment 2

[0021] A. In a 10L glass-lined reactor equipped with a stirrer, a thermometer, a vacuum pressure gauge, etc., add 4725g of acetonitrile and 189g of compound (Ⅲ) under stirring, cool down to 10°C, add 168g of potassium hydroxide powder, and replace the air with nitrogen , keep stirring and react for 2 hours. Then add 477.2g of pyridine-3-sulfonyl chloride dropwise to the reaction solution, control the reaction temperature at 30±2°C, keep the temperature and stir for 0.5 hours, filter the reaction mixture into the still, and recover the solvent by distillation under reduced pressure until there is no distillate Until the internal temperature is controlled below 50°C, the vacuum degree is ≥-0.07MPa, after the concentration is completed, add 405g of ethyl acetate and 2430g of n-hexane, add 11.3g of activated carbon under stirring, heat up to 70°C for decolorization for 0.5 hours, press filter, cool down and crystallize Heat it at 3°C ​​for 1.5 hours to crystallize, centrifuge, and...

Embodiment 3

[0024] A. In a 10L glass-lined reactor equipped with a stirrer, a thermometer, a vacuum pressure gauge, etc., add 2835g of acetonitrile and 189g of compound (Ⅲ) under stirring, cool down to 12°C, add 84g of potassium hydroxide powder, and replace the air with nitrogen , keep stirring and react for 2 hours. Add 238.6g of pyridine-3-sulfonyl chloride dropwise to the reaction, control the reaction temperature at 30±2°C, keep the temperature and stir for 1.5 hours, filter the reaction mixture into the still, and recover the solvent by distillation under reduced pressure until there is no distillate , the internal temperature is controlled below 50°C, the vacuum degree is ≥-0.07MPa, after the concentration is completed, add 472.5g of ethyl acetate and 1417.5g of n-hexane, add 9.5g of activated carbon under stirring, heat up to 75°C for 0.5 hours of decolorization, press filter, and cool down The crystallization was carried out at 0° C., incubated for 1 hour, centrifuged, and vacuum...

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Abstract

The invention provides a preparation and purification method of a key intermediate, 5-(2-fluorophenyl)-1-(pyridine-3-ylsulfonyl)-1H-pyrrole-3-formaldehyde compound (I), for preparing a chemical drug fluorine prazan for treating gastric ulcer, duodenal ulcer and reflux esophagitis. The preparation and purification method is especially suitable for removing the incompletely reacted raw material compound (III) remaining in the target compound (I) for purification, effectively reduces the impurity content, and improves the quality of the subsequent target product. The method is stable in process,simple to operate, easy to control in process conditions, simple and convenient in post-treatment, less in three wastes, good in product quality, high in yield, low in production cost and suitable forindustrial production, and the mother liquor can be continuously recycled.

Description

technical field [0001] The invention belongs to the field of chemical synthesis and preparation, in particular to a preparation and purification method of 5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbaldehyde (I). Background technique [0002] The preparation method of 5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbaldehyde (I) reported in the existing literature has: CN 1O492679OA application published a In the high-purity vonoPrazan Fumarate compound and its intermediates, impurities, and their preparation methods, 5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H -Pyrrole-3-carboxaldehyde crude product refining, the effect of this refining method is unsatisfactory, the purity of the obtained refined product is low, the HPLC content is less than 98%, and there are many known impurities and unknown impurities and the content is relatively high. The synthetic method reported in the patent WO2007026916 uses 5-(2-fluorophenyl)-1H-pyrrole-3-carbaldeh...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/12
CPCC07D401/12
Inventor 朱连博郑忠辉
Owner SHANDONG XINHUA PHARMA CO LTD
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