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A kind of preparation method of amide compound

A technology of amide compounds and compounds, which is applied in the field of organic compound preparation, can solve problems such as difficult control of reaction progress, and achieve the effects of simple and controllable preparation process, short synthetic route, and easy industrialization

Active Publication Date: 2016-03-30
苏州纳凯科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Under alkaline conditions, the hydrogen peroxide oxidation method can hydrolyze nitriles into amides in a short period of time at room temperature; but this method is usually not easy to control the progress of the reaction, and the cyano group is completely hydrolyzed into carboxylic acid

Method used

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  • A kind of preparation method of amide compound

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Experimental program
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Effect test

Embodiment 1

[0029] 2-bromo-5-cyanopyridine (10mmol, 1.83g), 2,4-difluorophenylboronic acid (10mmol, 1.58g), Na 2 CO 3 (0.5mmol, 57mg), tetrakistriphenylphosphopalladium (0.1mmol, 115mg) was dissolved in a mixed solvent of toluene / ethanol / water (V:V:V=5:2:1), and after reflux reaction for 24 hours, Stop the reaction, let stand at room temperature, wash with dichloromethane, collect the organic phase, and then use silica gel column chromatography to purify and separate to obtain a white solid 2-(2',4'-difluorophenyl)-5- Aminopyridine 2.1g (yield: 89%); Ms (M / Z): 234.1 (M + ); 1 HNMR (DMSO- d 6 ,400MHz), δppm:9.15(s,1H),8.33(dd,J=8Hz,2Hz,1H),8.22(s,1H),8.06(m,1H),7.88(m,1H),7.66(s ,1H),7.44(m,1H),7.27(m,1H).

Embodiment 2

[0031] 2-bromo-5-cyanopyridine (1mmol, 0.183g), phenylboronic acid (1mmol, 0.122g), K 2 CO 3 (0.1mmol, 13.8mg), tetrakistriphenylphosphopalladium (0.01mmol, 11.5mg) was dissolved in a mixed solvent of tetrahydrofuran / water (V:V=3:1), and after reflux reaction for 12 hours, the reaction was stopped and static After placing at room temperature, after washing with dichloromethane, the organic phase was collected, and then purified and separated by silica gel column chromatography to obtain 0.12 g of white solid 2-phenyl-5-amidopyridine (yield: 60%); Ms (M / Z):198.2(M + ).

Embodiment 3

[0033] 2-bromo-5-cyanopyridine (1mmol, 0.183g), 3-methoxy-phenylboronic acid (1mmol, 0.152g), Na 2 CO 3 (0.1mmol, 11.4mg), tetrakistriphenylphosphopalladium (0.1mmol, 11.5mg) was dissolved in a mixed solvent of toluene / water (V:V=2:1), and after reflux reaction for 36 hours, the reaction was stopped and static After placing at room temperature and washing with dichloromethane, the organic phase was collected, purified and separated by silica gel column chromatography to obtain 0.19 g of white solid 2-(3'-methoxyphenyl)-5-amidopyridine ( Yield: 83%); Ms(M / Z): 228.0(M + ).

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Abstract

The invention discloses a preparation method of an amide compound, which specifically comprises the following steps: in an air atmosphere, in the presence of a base, using a cyano compound and a boric acid compound as raw materials, and using a mixed solvent of a protic solvent and an aprotic solvent as the reaction The medium uses a palladium compound as a catalyst to prepare an amide compound through a cyano hydrolysis reaction and a carbon-carbon coupling reaction under heating. The new method for preparing amide compounds disclosed in the present invention avoids the use of oxidizing agents in the prior art, thereby effectively inhibiting the excessive hydrolysis of cyano groups, avoiding the further hydrolysis of amides into carboxylic acids, and greatly improving the reaction of amide compounds yield; and this method can be carried out simultaneously with the carbon-carbon coupling reaction to prepare more amide compounds, which has important market value and economic benefits for the industrial production of amide compounds.

Description

technical field [0001] The invention belongs to the field of organic compound preparation, and in particular relates to a preparation method of amide compounds. Background technique [0002] Amide compounds are an important class of chemical raw materials, which are widely used in the fields of biology, medicine, and pharmacy. There are two ways to prepare amide compounds in the prior art: one is to prepare amides through the condensation reaction of carboxyl and amino groups, but this reaction usually requires activation of raw materials, and the reaction conditions are usually relatively harsh. [0003] In addition, amide compounds are prepared by hydrolysis of cyano group, which is mainly divided into hydrolysis of cyano group under acidic or alkaline conditions. Under alkaline conditions, the hydrogen peroxide oxidation method can hydrolyze nitriles to amides in a short period of time at room temperature; but this method is usually not easy to control the progress of th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/82C07D213/81
CPCC07D213/81C07D213/82
Inventor 周宇扬王筱梅叶常青朱赛江梁作芹
Owner 苏州纳凯科技有限公司
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