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Ruthenium-Catalyzed Ortho-Meta Selective Hydrogen-Deuterium Exchange Reaction of Benzene Ring

A technology of reaction and benzene ring, which is applied in the field of ruthenium-catalyzed ortho-meta-selective hydrogen-deuterium exchange reaction of benzene ring, which can solve the problems of large manpower and material resources

Active Publication Date: 2022-04-05
RENMIN UNIVERSITY OF CHINA
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The existing method, on the one hand, can only introduce two deuterium atoms at most, which is not conducive to the application in the field of analysis and detection; Design, which requires a lot of manpower and material resources

Method used

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  • Ruthenium-Catalyzed Ortho-Meta Selective Hydrogen-Deuterium Exchange Reaction of Benzene Ring
  • Ruthenium-Catalyzed Ortho-Meta Selective Hydrogen-Deuterium Exchange Reaction of Benzene Ring
  • Ruthenium-Catalyzed Ortho-Meta Selective Hydrogen-Deuterium Exchange Reaction of Benzene Ring

Examples

Experimental program
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Embodiment Construction

[0022] The experimental methods used in the following examples are conventional methods unless otherwise specified.

[0023] The materials and reagents used in the following examples can be obtained from commercial sources unless otherwise specified.

[0024] The reaction equation is shown in the following formula:

[0025]

[0026] Follow the steps below to prepare deuterated compounds:

[0027] Add clean magnets of appropriate size to a dry sealed tube, then weigh 0.2mmol of the raw material (compound shown in formula II), add it to the sealed tube, and then weigh 0.005mmol of dichlorobis(4-methyliso Propylphenyl) ruthenium, 0.03 mmol silver acetate and 0.03 mmol triphenylphosphine were added to the sealed tube. After replacing the nitrogen atmosphere in the sealed tube, add 0.8ml [D 4 ] - Acetic acid, sealed. The reaction system was refluxed at 150°C for 24 hours. After the reaction, sodium bicarbonate and water were added to the reaction system, stirred until no bub...

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Abstract

The invention discloses a ruthenium-catalyzed selective hydrogen-deuterium exchange reaction in the ortho-meta position of a benzene ring. Specifically, the present invention provides a preparation method for a deuterium-labeled compound shown in formula I, comprising the following steps: under the catalysis of dichlorobis(4-methylisopropylphenyl)ruthenium, in silver acetate and triphenylphosphine Under the condition of existence, the compound represented by formula II reacts with deuterated acetic acid to obtain the deuterium-labeled compound represented by formula I. The present invention adopts dichlorobis(4-methylisopropylphenyl) ruthenium as a catalyst, which broadens the scope of application of the guiding group, and is not limited to groups such as pyrazole and pyridine, such as other azaaromatic rings, such as : Pyrazine, pyrimidine, benzimidazole, etc., can well induce the efficient exchange of hydrogen and deuterium at the ortho and meta positions of the benzene ring, and the highest deuteration rate can reach 95%. The reaction of the invention can realize the deuterium substitution of the adjacent meta-position of the benzene ring at the same time, can introduce multiple deuterium atoms, provides another simple and efficient method for the synthesis of the internal standard reagent, and has high social and economic benefits.

Description

technical field [0001] The invention relates to a ruthenium-catalyzed ortho-meta-selective hydrogen-deuterium exchange reaction of a benzene ring, which belongs to the field of organic synthesis. Background technique [0002] Deuterium-labeled compounds have very important applications in the fields of organic reaction mechanism analysis, analytical testing, material science, life science, and medicine. Isotope dilution mass spectrometry based on deuterium-labeled compounds has been widely used in quantitative analysis. It is less affected by matrix effects and has the advantages of fast, accurate, high sensitivity and good repeatability. Deuterium-labeled drug molecules are also widely used in the analysis of drug metabolism process and clinical pharmacokinetic research. The benzene ring is one of the most widely existing frameworks in natural products and drug molecules, so the deuteration of the benzene ring, especially the selective deuteration, has always been the focu...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07B59/00C07D213/127C07D213/16C07D231/12C07D235/18C07D241/12
CPCC07B59/002C07D231/12C07D213/16C07D213/127C07D235/18C07D241/12C07B2200/05
Inventor 闫晓宇赵亮亮
Owner RENMIN UNIVERSITY OF CHINA
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