Preparation method of 2-trifluoromethyl substituted imidazole compound

The technology of imidazole compound and trifluoromethyl group is applied in the field of preparation of imidazole compound, can solve problems such as not being widely used, and achieve the effects of good reaction applicability, strong practicability, and cheap and easy-to-obtain reaction raw materials

Active Publication Date: 2020-07-17
ZHEJIANG SCI-TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, the more commonly used trifluoromethyl synthons are trifluorodiazoethane and trifluoroethylimidoyl halide. The latter is not widely used at present, but it has great application potential and needs to be further studied. Research

Method used

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  • Preparation method of 2-trifluoromethyl substituted imidazole compound
  • Preparation method of 2-trifluoromethyl substituted imidazole compound
  • Preparation method of 2-trifluoromethyl substituted imidazole compound

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Embodiment Construction

[0036] The present invention will be further described below in conjunction with specific embodiments.

[0037] Add palladium chloride, triphenylphosphine, acetic anhydride and formic acid mixture, sodium bicarbonate, trifluoroethylimidoyl chloride (II), propargylamine (III), Diaryliodonium salt (IV) and 2 mL of organic solvent, mixed and stirred evenly, reacted for 16-24 hours according to the reaction conditions in Table 2, filtered, mixed with silica gel, purified by column chromatography to obtain the corresponding 2-trifluoromethyl substituted The imidazole compound (I), the reaction process is shown in the following formula:

[0038]

[0039] The raw material addition of table 1 embodiment 1~15

[0040]

[0041]

[0042] Table 2

[0043]

[0044] In Table 1 and Table 2, T is the reaction temperature, t is the reaction time, Ph is phenyl, Me is methyl, OMe is methoxy, t-Bu is tert-butyl, NO 2 for nitro, CF 3 is trifluoromethyl, THF is tetrahydrofuran.

[...

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Abstract

The invention discloses a preparation method of a 2-trifluoromethyl substituted imidazole compound. The preparation method comprises the following steps: adding a palladium catalyst, a ligand, a carbon monoxide substitute, an additive, trifluoroethyl imine acyl chloride, propargylamine and diaryliodonium salt into an organic solvent, carrying out a reaction at 30 DEG C for 18-20 h, and after the reaction is completed, carrying out post-treatment to obtain the 2-trifluoromethyl substituted imidazole compound. The preparation method has the advantages of simple operation, cheap and easily available initial raw materials, high reaction efficiency, good substrate compatibility, realization of synthesis of diversified substituted trifluoromethyl-containing imidazole compounds through substratedesign, convenience in operation, and widening of the practicality of the method.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a preparation method of a 2-trifluoromethyl-substituted imidazole compound. Background technique [0002] Imidazole compound is an important nitrogen-containing five-membered heterocyclic ring, which widely exists in various molecular frameworks with important biological activities (Med.Res.Rev.2014,34,340-437). Many drugs and functional material molecules contain imidazole molecular structure. Imidazole compounds can also be used as ionic liquids and ligands to coordinate with metals, and are often used in the field of coordination catalysis (Chem. Soc. Rev. 2017, 46, 4845-4854). The introduction of trifluoromethyl groups into heterocyclic molecules has many advantages, and can significantly improve the electronegativity, bioavailability, metabolic stability, and lipophilicity of the parent molecule (J. Med. Chem. 2015, 58, 8315-8359). [0003] [0004] The method of synthe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/64
CPCC07D233/64
Inventor 吴小锋陈铮凯王伟丰杨合肥
Owner ZHEJIANG SCI-TECH UNIV
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