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Methyl aryl thioether compound, and synthetic method and applications thereof

A technology of methyl aryl sulfide and synthesis method, which is applied in the formation/introduction of mercapto/thioether groups, thioether preparation, drug combination, etc., can solve the problems of high economic cost and low atom utilization rate of methyl iodide, Achieve the effects of high yield, simple reaction operation and mild reaction conditions

Inactive Publication Date: 2017-06-20
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Methyl iodide is economically costly and has low atomic utilization

Method used

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  • Methyl aryl thioether compound, and synthetic method and applications thereof
  • Methyl aryl thioether compound, and synthetic method and applications thereof
  • Methyl aryl thioether compound, and synthetic method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044]

[0045] Under a nitrogen atmosphere, the substrate fenofibrate 1a (0.2mmol, 72.2mg), KSAc (0.6mmol, 68.4mg), DMC (1.0mmol, 90mg), Pd(OAc) was added to a 25mL test tube reactor 2 (0.01mmol, 2.3mg), PPh 3 (0.02mmol, 5.9mg), tBuOK (0.6mmol, 69.2mg), and DMSO (2.0mL). The reaction system was heated to 120°C for reaction. After the reaction was detected by TLC, the system was cooled to room temperature. The reaction was quenched with saturated ammonium chloride aqueous solution, extracted with ethyl acetate (3*10mL), and purified by column chromatography to obtain 62.5 mg (84%) of product 2a. Rf=0.40 (petroleum ether: ethyl acetate=10:1 ); 1 H NMR (400MHz, CDCl 3 ): δ7.73(d, J=9.2Hz, 2H), 7.70(d, J=8.8Hz, 2H), 7.29(d, J=8.4Hz, 2H), 6.87(d, J=8.8Hz, 2H ),5.14‐5.04(m,1H),2.53(s,3H),1.66(s,6H),1.21(s,3H),1.99(s,3H); 13 C NMR (400MHz, CDCl 3 ): δ194.5, 173.1, 159.4, 144.5, 134.2, 131.7, 130.8, 130.3, 124.9, 117.2, 79.3, 69.2, 25.3, 21.5, 14.9; ,1151,837,761cm ‐1 ; HR...

Embodiment 2

[0047]

[0048] Under a nitrogen atmosphere, the substrate fenofibrate 1a (0.2mmol, 72.2mg), KSAc (0.6mmol, 68.4mg), DMC (1.0mmol, 90mg), Pd(OAc) was added to a 25mL test tube reactor 2 (0.01mmol, 2.3mg), tBuOK (0.6mmol, 69.2mg), and DMSO (2.0mL). The reaction system was heated to 100°C for reaction. After the reaction was detected by TLC, the system was cooled to room temperature. The reaction was quenched with saturated ammonium chloride aqueous solvent, extracted with ethyl acetate (3*10 mL), and purified by column chromatography to obtain 31.2 mg (42%) of product 2a. The analytical data were the same as in Example 1.

Embodiment 3

[0050]

[0051] Under a nitrogen atmosphere, the substrate fenofibrate 1a (0.2mmol, 72.2mg), KSAc (0.6mmol, 68.4mg), DMC (1.0mmol, 90mg), Pd(OAc) was added to a 25mL test tube reactor 2 (0.01mmol, 2.3mg), tBuONa (0.6mmol, 57.6mg), and DMSO (2.0mL). The reaction system was heated to 100°C for reaction. After the reaction was detected by TLC, the system was cooled to room temperature. The reaction was quenched with saturated ammonium chloride aqueous solvent, extracted with ethyl acetate (3*10 mL), and purified by column chromatography to obtain 45.4 mg (61%) of product 2a. The analytical data were the same as in Example 1.

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Abstract

The invention discloses a methyl aryl thioether compound represented by formula 2, and a synthetic method and applications thereof. According to the synthetic method, in a reaction solvent, an aryl halide or an aromatic halide, dimethyl carbonate, and potassium thioacetate are taken as reaction raw materials, reaction is carried out in the presence of metal palladium catalyst under the action of a ligand and an alkali so as to obtain the methyl aryl thioether compound. The reaction conditions of the synthetic method are mild; the raw materials are cheap and easily available; reaction operation is simple; yield is relatively high. The methyl aryl thioether compound can be used for providing skeleton structures for the synthesis of a plurality of natural products and medicines, and can be widely applied in industrialized large-scale production.

Description

technical field [0001] The invention relates to a method for synthesizing methyl aryl sulfide compounds, belonging to the technical field of organic compound technology application. Background technique [0002] Carbon-sulfur bonds are widely found in life molecules, natural products, food and medicine, materials and pesticides. Taking drugs as an example, sulfur-containing molecular skeletons are often used in antibacterial, antiviral, anticancer and other drug molecules. Arylmethyl sulfide drugs and their corresponding sulfone and sulfoxide drugs have shown their unique importance in modern medicine, as shown in the following structural formula: [0003] [0004] There are two main ways to construct methyl sulfide compounds in traditional methods. One is the direct introduction of methyl sulfide compounds. Representative compounds include methyl mercaptan and sodium methyl mercaptide. Methyl mercaptan has a low boiling point, foul smell, and can paralyze the central n...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B45/06C07C321/28C07C319/14C07D213/85C07D215/36C07D237/18C07D487/04C07D239/93C07D217/22C07D239/58C07D241/18C07D495/04C07D251/46C07H19/167C07D251/52C07D213/40A61P31/04A61P31/12A61P35/00
CPCC07B45/06C07C321/28C07D213/40C07D213/85C07D215/36C07D217/22C07D237/18C07D239/58C07D239/93C07D241/18C07D251/46C07D251/52C07D487/04C07D495/04C07H19/167
Inventor 姜雪峰乔宗君
Owner EAST CHINA NORMAL UNIV
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