Method for preparing chemical compounds of interest by aromatic nucleophilic substitution

A technology of aromatics and compounds, applied in the field of chemical synthesis, can solve problems such as inability to handle and produce

Inactive Publication Date: 2013-03-06
曼恩大学
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Furthermore, the Myers reaction does not work with compounds 3 that contain C6 substituents other than hydrogen: the protected carboxyl groups of these compounds are completely inert to hydrolysis and thus cannot yield 4

Method used

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  • Method for preparing chemical compounds of interest by aromatic nucleophilic substitution
  • Method for preparing chemical compounds of interest by aromatic nucleophilic substitution
  • Method for preparing chemical compounds of interest by aromatic nucleophilic substitution

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Experimental program
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no. 1 approach

[0081] According to a first embodiment, Nu is not a substituted or unsubstituted amine, especially not an aniline derivative, more especially not 4-[2-(3,4, when the fluorine or chlorine atom is located in the ortho position of the acid function. -Dichlorophenyl)ethyl]aniline.

[0082] According to a second embodiment, Nu is not a substituted or unsubstituted amine when the fluorine atom is located ortho to the acid function.

[0083] According to one embodiment of the present invention, in compound (II), the leaving group (R1 or R2) is a fluorine or chlorine atom, and the nucleophile of the compound of general formula NuM is an aniline derivative. In this embodiment, according to the first aspect, the NuM compound is obtained according to the synthesis described below, with the proviso that NuM is not a reaction product between a nucleophile and a metal base selected from lithium hydride, sodium hydride , potassium hydride, calcium hydride, lithium diisopropylamide, lithium ...

Embodiment

[0128] All reactions were performed in anhydrous solvents under an inert atmosphere (Gordon, J.A.; Ford, R.A. The Chemist's Companion, Wiley J. and Sons, New York, 1972). THF was distilled over anhydrous THF GTS100 bench (Glass Technology). Alkyllithium derivatives are periodically titrated with N-benzylbenzamide (Burchat, A.F.; Chong, J.M.; Nielsen, N.J. Organomet. Chem. 1997, 542, 281).

[0129] S-butyllithium (1.4M solution in cyclohexane), n-butyllithium (1.6M solution in hexane), tert-butyllithium (1.7M solution in pentane) and phenyllithium (1.8M solution in dibutyl ether) were prepared by Sold by Acros Chemicals and Aldrich Chemical Company.

[0130] Ethylmagnesium bromide (3M in diethyl ether) and vinylmagnesium bromide (1M in THF) are sold by Acros Chemicals and Aldrich Chemical Company.

[0131] Amines in CaH 2 Distilled and stored under argon atmosphere.

[0132] proton 1 H (400MHz or 200MHz) and Carbon 13NMR spectra of C (50 MHz or 100.6 MHz) were recorded on...

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Abstract

The aim of the invention is to provide a method for preparing carboxylic acid derivatives by aromatic nucleophilic substitution, in which a carboxylic acid derivative having a single carboxyl functional group, or one of the salts thereof, said carboxylic acid derivative having, in the ortho position of the carboxyl functional group, a leaving group, which is preferably an atom of fluorine or of chlorine or an alkoxy group, chiral or not, preferably a methoxy group, said carboxylic acid derivative not being substituted by an electroattractive group other than the leaving group if any; is reacted with a reactant MNu, where M is a metal and Nu is a nucleophile, chiral or not, said aromatic nucleophilic substitution reaction being carried out without a catalyst and without a step of protecting / deprotecting the acid functional group of the starting compound.

Description

technical field [0001] The present invention relates to the field of chemical synthesis, and in particular, the present invention proposes a method capable of performing nucleophilic aromatic substitution on aromatic carboxylic acid derivatives in the absence of a catalyst, in particular but not exclusively to form symmetric or A novel approach to asymmetric biaryls. Background technique [0002] Nucleophilic aromatic substitution reactions are a widely used chemical reaction during which atoms attached to aromatic rings are replaced by nucleophilic groups. A wide variety of aromatic compounds, especially pharmaceutically active ingredients such as biphenyl, can thus be prepared. [0003] Nucleophilic aromatic substitution reactions performed on an industrial scale are usually carried out in the presence of catalysts comprising noble metals, especially palladium. However, to improve patient safety, pharmaceutical regulations have become much more stringent in recent years,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/353C07C227/08C07D295/155C07C229/56C07C229/58C07C229/64C07C229/68
CPCC07D295/155C07C227/08C07C51/367C07C51/353C07C63/36C07C63/66C07C65/24C07C229/56C07C229/58C07C229/64C07C229/68
Inventor 雅克·莫尔捷安-苏菲·卡斯塔奈迈克尔·比罗德-罗特尔
Owner 曼恩大学
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