Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

A kind of synthetic method of 4-(difluoromethyl)-2-hydroxypyridine-5-sulfonyl chloride

A synthesis method and hydroxypyridine technology, applied in the direction of organic chemistry, etc., to achieve the effects of easy realization, high selectivity and mild reaction conditions

Active Publication Date: 2022-04-05
埃法姆(常州)生命科学技术有限公司
View PDF4 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In view of this, we propose a synthetic method for the preparation of novel fluorine-containing pyridine intermediates, which has not been reported so far

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A kind of synthetic method of 4-(difluoromethyl)-2-hydroxypyridine-5-sulfonyl chloride
  • A kind of synthetic method of 4-(difluoromethyl)-2-hydroxypyridine-5-sulfonyl chloride
  • A kind of synthetic method of 4-(difluoromethyl)-2-hydroxypyridine-5-sulfonyl chloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] (1) Synthesis of Compound B

[0027] 5-Bromo-2-methoxypyridine (23g, 120mmol, 1eq.) was dissolved in 250ml of anhydrous tetrahydrofuran and set aside. Diisopropylamine (13.6g, 132mmol, 1.1eq.) was dissolved in 100ml of anhydrous tetrahydrofuran, cooled to -5°C, under nitrogen protection, n-butyl lithium (52.8ml, 132mmol, 1.1eq.) was added dropwise into the above solution. After completion of the dropwise addition, the mixture was stirred for 30 minutes.

[0028] The temperature of the above reaction system was lowered to -78°C, and a tetrahydrofuran solution of 5-bromo-2-methoxypyridine was added dropwise. After completion of the dropwise addition, the mixture was stirred for 1 hour. Then, N,N-dimethylformamide (13.4 g, 180 mmol, 1.5 eq.) was added dropwise to the above reaction system, and reacted for 2 hours.

[0029] After the reaction finished, slowly add 120ml of ammonium chloride solution in the reaction solution. It was extracted with n-hexane, and the organ...

Embodiment 2

[0044] (1) Synthesis of Compound B

[0045] 5-Bromo-2-methoxypyridine (28.8g, 150mmol, 1eq.) was dissolved in 300ml of anhydrous tetrahydrofuran and set aside. Dissolve diisopropylamine (17g, 165mmol, 1.1eq.) in 150ml of anhydrous tetrahydrofuran, cool to -5°C, and add n-butyllithium (66ml, 165mmol, 1.1eq.) dropwise to the above-mentioned in solution. After completion of the dropwise addition, the mixture was stirred for 30 minutes.

[0046] The temperature of the above reaction system was lowered to -78°C, and a tetrahydrofuran solution of 5-bromo-2-methoxypyridine was added dropwise. After completion of the dropwise addition, the mixture was stirred for 1 hour. Then, N,N-dimethylformamide (16.8 g, 225 mmol, 1.5 eq.) was added dropwise to the above reaction system, and reacted for 2 hours.

[0047] After the reaction finished, slowly add 150ml ammonium chloride solution in the reaction solution. It was extracted with n-hexane, and the organic phase was dried over anhydrous...

Embodiment 3

[0062] (1) Synthesis of Compound B

[0063] 5-Bromo-2-methoxypyridine (17.3g, 90mmol, 1eq.) was dissolved in 200ml of anhydrous tetrahydrofuran and set aside. Diisopropylamine (10.2g, 99mmol, 1.1eq.) was dissolved in 80ml of anhydrous tetrahydrofuran, cooled to -5°C, under nitrogen protection, n-butyl lithium (39.6ml, 99mmol, 1.1eq.) was added dropwise into the above solution. After completion of the dropwise addition, the mixture was stirred for 30 minutes.

[0064] The temperature of the above reaction system was lowered to -78°C, and a tetrahydrofuran solution of 5-bromo-2-methoxypyridine was added dropwise. After completion of the dropwise addition, the mixture was stirred for 1 hour. Then, N,N-dimethylformamide (10.1 g, 135 mmol, 1.5 eq.) was added dropwise to the above reaction system, and reacted for 2 hours.

[0065] After the reaction finished, slowly add 100ml of ammonium chloride solution in the reaction solution. It was extracted with n-hexane, and the organic...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention provides a method for synthesizing 4-(difluoromethyl)-2-hydroxypyridine-5-sulfonyl chloride, which belongs to the field of organic chemical synthesis. Mainly comprising the following steps: compound B is reacted with diethylaminosulfur trifluoride to obtain compound C; compound C is reacted with sodium iodide and trimethylchlorosilane to obtain compound D; under the action of alkali and catalyst, compound D React with benzyl mercaptan, 4,5-bisdiphenylphosphine-9,9-dimethylxanthene to obtain compound E; react compound E with N-chlorosuccinimide to obtain the final product compound F . The method has high selectivity, mild reaction conditions, simple synthesis operation and easy realization. In the above synthesis process, compound B is a self-made synthetic material, using 5-bromo-2-methoxypyridine as a raw material, and compound B is obtained through a nucleophilic substitution reaction.

Description

technical field [0001] The invention relates to the field of organic chemical synthesis, in particular to a synthesis method of 4-(difluoromethyl)-2-hydroxypyridine-5-sulfonyl chloride. Background technique [0002] Fluorinated pyridines are important pharmaceutical intermediates. At present, a variety of fluorine-containing compounds have been applied in the fields of pesticides and medicines. For example, fluazinam is a high-efficiency, low-toxic, broad-spectrum fungicide with insecticidal activity, which can kill mosquitoes and flies, and is safe for humans, livestock, poultry, and fish. In terms of medicine, there is talniflumate, and there is also a yellow dye intermediate, and 2,6-difluoro-3-nitropyridine has a bactericidal effect, and it has an anti-caries effect as a chewing gum additive. [0003] Using simple pyridine compounds as raw materials, introduce difluoromethyl groups that regulate lipophilicity in organisms, strong electron-donating hydroxyl groups, or s...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/71
CPCC07D213/71
Inventor 史建云许义波戴红升周超
Owner 埃法姆(常州)生命科学技术有限公司
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com