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Synthetic method of 5-fluoro-3-pyridine sulfonyl chloride

A technology of pyridinesulfonyl chloride and synthesis method is applied in the field of synthesis of pharmaceutical intermediate 5-fluoro-3-pyridinesulfonyl chloride, and can solve the problems of difficulty in amplification, poor applicability, complicated post-processing and the like

Active Publication Date: 2012-05-16
WUXI APPTEC (TIANJIN) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The purpose of the present invention is to provide a novel synthesis method of 5-fluoro-3-pyridinesulfonyl chloride, which mainly solves the lack of existing synthetic routes and existing reaction routes through a method of quickly and efficiently introducing sulfonyl chloride on the pyridine ring. The reagent smells bad, the post-processing is complicated, the amplification is difficult, the applicability is not wide and other technical problems

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0014] 5-fluoro-3-bromo-pyridine 1 (45g, 0.256mol) was added into tetrahydrofuran (250mL), and then a solution of isopropylmagnesium bromide in tetrahydrofuran (128mL, 0.256mol, 2Min tetrahydrofuran) was slowly added dropwise at 30°C. Stirring was continued for 2 hours after the dropwise addition was complete. It was then cooled to -40°C with an ice-acetone solution and fed with sulfur dioxide gas. After 2 hours, the bubbling ceased and sulfuryl chloride (41.4 g, 0.307 mol) was added slowly maintaining the temperature at -40°C. After the addition was complete it was allowed to warm slowly to room temperature (20-30°C) and stirred for an additional 2 hours. After the detection found that the raw materials had completely disappeared, 0.5 L of water was added to the reaction system, and extracted with ethyl acetate (250 mL*3). The combined organic phases were washed with saturated brine, dried over anhydrous sodium sulfate, filtered to remove the desiccant, and the filtrate wa...

Embodiment 2

[0017] 5-fluoro-3-bromo-pyridine 1 (17.6g, 0.1 mol) was added to diethyl ether (100mL), and then a tetrahydrofuran solution of isopropylmagnesium bromide (50mL, 0.1mol, 2 Min tetrahydrofuran) was slowly added dropwise at 25°C. Stirring was continued for 0.5 hours after the dropwise addition was complete. It was then cooled to -40°C with an ice-acetone solution and fed with sulfur dioxide gas. After 1 hour, the bubbling ceased and sulfuryl chloride (16.2 g, 0.12 mol) was added slowly maintaining the temperature at -30°C. After the addition was complete it was allowed to warm slowly to room temperature (20-30°C) and stirred for a further 1 hour. After the detection found that the raw materials had completely disappeared, 0.2 L of water was added to the reaction system, and extracted with ethyl acetate (100 mL*3). The combined organic phases were washed with saturated brine, dried over anhydrous sodium sulfate, filtered to remove the desiccant, and the filtrate was concentrate...

Embodiment 3

[0019] 5-fluoro-3-bromo-pyridine 1 (17.6g, 0.1mol) was added to diethyl ether (100mL), and then a tetrahydrofuran solution of isopropylmagnesium bromide (50mL, 0.1 mol, 2 Min tetrahydrofuran) was slowly added dropwise at 20°C. Stirring was continued for 1.5 hours after the dropwise addition was complete. It was then cooled to -40°C with an ice-acetone solution and fed with sulfur dioxide gas. After 2 hours, the bubbling ceased and sulfuryl chloride (16.2 g, 0.12 mol) was added slowly maintaining the temperature at -40°C. After the addition was complete it was allowed to warm slowly to room temperature (20-30°C) and stirred for an additional 2 hours. After the detection found that the raw materials had completely disappeared, 0.2 L of water was added to the reaction system, and extracted with ethyl acetate (100 mL*3). The combined organic phases were washed with saturated brine, dried over anhydrous sodium sulfate, filtered to remove the desiccant, and the filtrate was conce...

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Abstract

The invention relates to a synthetic method of 5-fluoro-3-pyridine sulfonyl chloride. In the invention, a method of quickly and efficiently introducing sulfonyl chloride into a pyridine ring is mainly used for solving the existing technical problems of lack of synthetic routes, smelly reaction route reagents, complicated post-treatment, difficulty in amplification, limited applicability and the like. The synthetic method comprises the following steps of: taking 5-fluoro-3-bromine-pyridine 1; firstly adding isopropyl magnesium bromide for reacting to obtain 5-fluoro-3-pyridine magnesium bromide 2; then introducing sulfur dioxide gas; and finally treating with sulfonyl chloride to obtain the finished product, namely 5-fluoro-3-pyridine sulfonyl chloride 3. The synthetic routes in the invention can be used for quickly and conveniently preparing the 5-fluoro-3-pyridine sulfonyl chloride.

Description

technical field [0001] The invention relates to a method for synthesizing a novel pharmaceutical intermediate 5-fluoro-3-pyridinesulfonyl chloride. Background technique [0002] 5-Fluoro-3-pyridinesulfonyl chloride is a novel pharmaceutical intermediate, because it has both fluorine atoms and sulfonyl chloride on its molecule, it can be widely used in the design of drug molecules; its sulfonyl chloride group can be combined with Many other drug template molecules react to synthesize various drug molecules with different needs, such as various sulfonamides. Its fluorine atom group can also be used as a leaving group in a nucleophilic reaction to react with many drug template molecules to synthesize various drug molecules with different requirements. WO2010 / 24451 A1 reported that the drug molecule combined with the compound has the application as a proton pump inhibitor for the treatment of acid-related diseases. Therefore, 5-fluoro-3-pyridinesulfonyl chloride has broad rese...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/71
Inventor 柏祝陈先印贺海鹰陈曙辉
Owner WUXI APPTEC (TIANJIN) CO LTD
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