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

Alkyl modified aryl pyridine compound and preparation method thereof

A technology for arylpyridines and compounds, which is applied in the field of alkyl-modified arylpyridines and their preparation, can solve the problems of high price, side reactions, and low utilization of raw materials, and achieves simple operation, mild reaction conditions, and reduced The effect of chemical waste generation

Active Publication Date: 2018-12-18
TONGJI UNIV
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, on the one hand, most of the reaction substrates used in this type of reaction, such as organometallic reagents and organic halides, are expensive, or require multiple steps to synthesize, which increases the cost of the reaction.
On the other hand, such reagents will have side reactions of self-coupling during the reaction process, and at the same time, chemical waste will be produced due to a large number of leaving groups after the reaction, the utilization rate of raw materials is low, and the environment is polluted.

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
  • Alkyl modified aryl pyridine compound and preparation method thereof
  • Alkyl modified aryl pyridine compound and preparation method thereof
  • Alkyl modified aryl pyridine compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Palladium-Catalyzed Reaction of Arylpyridines with Iodobutane

[0031] Palladium catalyzed arylpyridine and iodobutane reaction synthetic alkyl substituted arylpyridine arene compound, comprises the following steps: in the Schlenk reaction tube of 35ml, add stirring bar successively, 0.45mg Pd(OAc) 2 (10mol%), the corresponding arylpyridine (0.2mmol), 91.0uL iodobutane (0.8mmol), 44.5mg (BnO) 2 PO 2 H (80mol%), 165.4mgAg 2 CO 3 (3.0equiv) and 1.0mL of t-AmylOH:CH 3 CN (9:1) organic solvent, then seal the reaction tube with a matching polytetrafluoroethylene stopper, and place it in a magnetic stirrer at 60°C for 12 hours. At the end of the reaction, the reaction tube was removed from the heating device and cooled to room temperature. The reaction solution was diluted with ethyl acetate and filtered through diatomaceous earth. The filtrate obtained after washing several times with ethyl acetate was concentrated with a rotary evaporator to obtain the crude product Pu...

Embodiment 2

[0164] Palladium-Catalyzed Reaction of 2-Phenylpyridine with Iodoalkane

[0165] Into a 35ml Schlenk reaction tube, add a stirring bar, 0.45mg Pd(OAc) 2 (10mol%), the corresponding 28.6uL 2-phenylpyridine (0.2mmol), iodoalkane (0.8mmol), 44.5mg (BnO) 2 PO 2 H (80mol%), 165.4mgAg 2 CO 3(3.0equiv) and 1.0mL of t-AmylOH:CH 3 CN (9:1) organic solvent, then seal the reaction tube with a matching polytetrafluoroethylene stopper, and place it in a magnetic stirrer at 60°C for 12 hours. At the end of the reaction, the reaction tube was removed from the heating device and cooled to room temperature. The reaction solution was diluted with ethyl acetate and filtered through diatomaceous earth. The filtrate obtained after washing several times with ethyl acetate was concentrated with a rotary evaporator to obtain the crude product Purify and isolate the corresponding butyl compound through silica gel plate, weigh to determine the yield, and use NMR and HRMS for qualitative detection....

Embodiment 3

[0216] 2-Phenylpyridine, iodobutane, dibenzyl phosphate, silver carbonate and Pd(TFA) 2 Mix at a molar ratio of 1:4:0.8:3:0.01, dissolve in the solvent tert-amyl alcohol, then seal the reaction tube with a matching polytetrafluoroethylene stopper, and place it in a magnetic stirrer at 80°C for 12 hours. At the end of the reaction, the reaction tube was removed from the heating device and cooled to room temperature. The reaction solution was diluted with ethyl acetate and filtered through diatomaceous earth. The filtrate obtained after washing several times with ethyl acetate was concentrated with a rotary evaporator to obtain the crude product The corresponding butyl compound was obtained by purification and isolation on a silica gel plate, and the yield was calculated by weighing. The final product is:

[0217]

[0218] The yields were 76% and 12%, respectively.

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 relates to an alkyl modified aryl pyridine compound and a preparation method thereof, wherein the structural formula of the aryl pyridine compound is specifically represented by the following formula defined in the specification, R is the substituent on the phenyl ring, and is H or at least contains one selected from substituents containing halogen, aryl, methyl or methoxy, and R<1>is one selected from alkane containing aryl, cyano, methoxy, n-butyl, isopropyl or o-phthalimido. The synthesis method of the alkyl modified aryl pyridine compound comprises: taking aryl pyridine, halogenated aromatic hydrocarbon, a ligand compound, an oxidizing agent and a catalyst, mixing, dissolving in an organic solvent, and carrying out a reaction by using a divalent palladium salt as a catalyst to obtain the alkyl modified aryl pyridine compound. Compared to the method in the prior art, the method of the present invention has advantages of mild conditions, good yield, simple operation and wide substrate application range.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to an alkyl-modified arylpyridine compound and a preparation method thereof. Background technique [0002] Compounds containing alkyl structures are important components of many biomedicines, natural products, and chemical materials. The main methods of constructing carbon-carbon bonds in traditional chemistry include nucleophilic addition, nucleophilic substitution and Friedel-Crafts reaction. The origin of modern coupling reactions can be traced back to the 1970s, and the major impact of this type of reaction on organic synthesis technology and its development in the past two decades have been generally recognized by everyone. However, on the one hand, most of the reaction substrates used in such reactions, such as organometallic reagents and organic halides, are expensive, or require multi-step synthesis, which increases the cost of the reaction. On the other hand, such reagent...

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): C07D213/16C07D213/127C07D213/26C07D213/50C07D213/30C07D401/10C07D213/57
CPCC07D213/127C07D213/16C07D213/26C07D213/30C07D213/50C07D213/57C07D401/10
Inventor 张扬会王晓玲
Owner TONGJI UNIV
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