Eureka AIR delivers breakthrough ideas for toughest innovation challenges, trusted by R&D personnel around the world.

Synthesis method of fluxapyroxad based on Suzuki reaction

A technology of fluconazole and a synthesis method, which is applied in the field of organic chemical synthesis of pesticide molecules, can solve the problems of high safety risk of fluconazole and the like, and achieves the effects of great commercial value and potential, low preparation cost and mild reaction conditions.

Pending Publication Date: 2021-09-17
深圳市谦陌通辰实验有限公司
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] Aiming at the deficiencies of the existing technology, in order to solve the problems of high safety risks in the synthesis of flufenapyramide, the present invention provides an independently designed and innovative synthesis method

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
  • Synthesis method of fluxapyroxad based on Suzuki reaction
  • Synthesis method of fluxapyroxad based on Suzuki reaction
  • Synthesis method of fluxapyroxad based on Suzuki reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment approach

[0017] According to one embodiment of the present invention, the synthesis method comprises the following steps:

[0018] S1. Condensation of 3-difluoromethyl-1-methyl-1-piperazole-4-carboxylic acid with 2-iodoaniline in organic solvent under the action of coupling reagent and 4-dimethylaminopyridine Reaction to generate 3-difluoromethyl-N-(2-iodophenyl)-1-methyl-1-piperazole-4-amide;

[0019] S2.3-Difluoromethyl-N-(2-iodophenyl)-1-methyl-1-piperazole-4-amide occurs in organic solvents in the presence of palladium metal catalysts and alkaline reagents Suzuki reaction to 3-difluoromethyl-1-methyl-N-[3'-4'-5'-trifluoro-(1,1'-biphenyl)-2-yl]-1-piperene Azol-4-amide, the product of flufenapyramide.

[0020] Preferably, in step S1, the coupling reagent is 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, and the organic solvent is dichloromethane; in step S2 Among them, the palladium metal catalyst is tetrakis(triphenylphosphine) palladium, the basic reagent is potass...

Embodiment 1

[0030]

[0031] Take a round bottom flask with a built-in stirring bar. To this was added 3-difluoromethyl-1-methyl-1-pyrazole-4-carboxylic acid (1.00 g, 5.70 mmol), 2-iodoaniline (1.50 g, 6.84 mmol), 1-(3-di Methylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.20 g, 6.27 mmol), 4-dimethylaminopyridine (0.84 g, 6.84 mmol) and dichloromethane (20 ml). The resulting mixture was stirred overnight at room temperature. After the completion of the reaction was monitored by TLC, distilled water (20 ml) was added to the reaction system. The organic phase was separated and the aqueous phase was washed 3 times with dichloromethane (20 ml). The organic phases were combined and evaporated to dryness, the resulting crude product was purified by column chromatography to give 3-difluoromethyl-N-(2-iodophenyl)-1-methyl-1-pyrazole- The 4-amide is pure, with a yield of 81%, and a purity calculated by H NMR spectrum of 91%.

Embodiment 2

[0033]

[0034] Take a round bottom flask with a built-in stirring bar. To this was added 3-difluoromethyl-N-(2-iodophenyl)-1-methyl-1-piperazole-4-amide pure (0.31 g, 0.82 mmol), 3,4,5-tris Fluorophenylboronic acid (0.17 g, 0.98 mmol), tetrakis(triphenylphosphine)palladium (300 mg), potassium carbonate (0.57 g, 4.10 mmol) and tetrahydrofuran (9 ml). The resulting mixture was heated to reflux under nitrogen atmosphere and reacted overnight. After the reaction was detected by thin layer chromatography, water (20 ml) and dichloromethane (50 ml) were added thereto, and stirred for 30 minutes. The organic phase was separated, washed with saturated ammonium chloride solution (10 ml), dried and concentrated to dryness. The obtained crude product was purified by column chromatography to obtain pure flufenapyroxad as a light yellow solid with a yield of 92% and a purity of 95% calculated by H NMR spectroscopy.

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 discloses a synthesis method of fluxapyroxad based on Suzuki reaction. Compared with the prior art, the method has the advantages that high-toxicity, flammable and explosive carbon monoxide gas is avoided, and a complicated palladium metal catalyst is prepared. According to the method, a tetra (triphenylphosphine) palladium catalyst which is relatively cheap and easy to obtain is used, and a fluxapyroxad product is prepared through a mild Suzuki reaction with high universality. The method disclosed by the invention has the characteristics of being integrally simple, economical, environment-friendly, safe and efficient, and has relatively high industrial application potential.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis of pesticide molecules, and specifically relates to the preparation and industrialization of flufenapyramide, a pesticide molecule, using a self-involved and innovative synthesis method. Background technique [0002] Fluxapyroxad is a succinate dehydrogenase inhibitor fungicide developed by BASF. It was first registered and launched in the UK market in 2011, and its global sales reached US$390 million in 2015. At present, the product has been registered and launched in Australia, Argentina, the United States, Canada, the European Union, Brazil and China. [0003] Fluxapyroxad has good long-term disabling activity against a variety of fungal diseases, and can effectively prevent major diseases of crops such as grains, soybeans, corn, rapeseed, sugar beets, peanuts, and cotton. The product prevents a range of fungal diseases, such as Septoria, Botrytis cinerea, Powdery mildew and Rhizocton...

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
IPC IPC(8): C07D231/14
CPCC07D231/14
Inventor 程彦霓邓博远其他发明人请求不公开姓名
Owner 深圳市谦陌通辰实验有限公司
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
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