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Preparation method of imidazopyridine compound

A technology for imidazopyridine and compound is applied in the field of preparation of imidazopyridine compounds, and achieves the effects of safe and simple operation, good adaptability and simple and easy method.

Inactive Publication Date: 2015-09-09
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, using propargyl ester and 2-aminopyridine as raw materials, under the catalysis of copper salt, there is no report on the one-step synthesis of imidazopyridine compounds by intermolecular propargyl amination and series cyclization reactions.

Method used

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  • Preparation method of imidazopyridine compound
  • Preparation method of imidazopyridine compound
  • Preparation method of imidazopyridine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] A kind of imidazopyridine compound is prepared by the following method:

[0039]Add 0.25 mmol 2-aminopyridine, 0.30 mmol 1-phenyl-2-propyne-1-acetate into a screw-top test tube with 2 ml of toluene, mix well and add 0.025 mmol cuprous chloride , stirred and reacted at 80°C for 5 hours, stopped heating and stirring, cooled to room temperature, removed the solvent by rotary evaporation under reduced pressure, and then separated and purified by column chromatography to obtain imidazopyridine compounds. The column chromatography eluent used was petroleum A mixed solvent of ether and ethyl acetate (the volume ratio of petroleum ether: ethyl acetate is 3:1), the yield is 85%.

Embodiment 2

[0041] A kind of imidazopyridine compound is prepared by the following method:

[0042] Add 0.25 mmol 2-aminopyridine and 0.35 mmol 1-phenyl-2-propyne-1-acetate into a screw-top test tube with 2 ml of toluene, mix well and add 0.030 mmol cuprous chloride , stirred and reacted at 100°C for 6 hours, stopped heating and stirring, cooled to room temperature, removed the solvent by rotary evaporation under reduced pressure, and then separated and purified by column chromatography to obtain imidazopyridine compounds. The column chromatography eluent used was petroleum A mixed solvent of ether and ethyl acetate (the volume ratio of petroleum ether: ethyl acetate is 1:1), the yield is 80%.

Embodiment 3

[0044] A kind of imidazopyridine compound is prepared by the following method:

[0045] Add 0.25 mmol 2-aminopyridine and 0.40 mmol 1-phenyl-2-propyne-1-acetate into a screw-top test tube with 2 ml of toluene, mix well and add 0.040 mmol cuprous chloride , stirred and reacted at 150°C for 3 hours, stopped heating and stirring, cooled to room temperature, removed the solvent by rotary evaporation under reduced pressure, and then separated and purified by column chromatography to obtain imidazopyridine compounds. The column chromatography eluent used was petroleum Mixed solvent of ether and ethyl acetate (the volume ratio of petroleum ether: ethyl acetate is 5:1), the yield is 83%.

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Abstract

The invention belongs to the technical field of organic chemical synthesis and discloses a preparation method of an imidazopyridine compound. The method comprises the following specific steps: adding an alkyne propyl ester compound and a 2-aminopyridine compound into an organic solvent and mixing uniformly; adding a copper salt catalyst, and stirring and reacting at 80-150 DEG C for 3-8 hours in an air atmosphere; and after the reaction is over, cooling to room temperature, performing reduced-pressure rotary evaporation and purifying through column chromatography to obtain the imidazopyridine compound. The method disclosed by the invention is safe and easy to operate, good in functional group adaptability, wide in substrate adaptability, environmentally friendly and is beneficial to industrial production, and can be widely applied to organic synthesis; the raw materials are cheap and easily available.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and in particular relates to a preparation method of imidazopyridine compounds. Background technique [0002] With the continuous development of social economy, the problems of globalized environmental pollution and energy consumption are becoming more and more serious, and solving the sustainable development of human beings has become an important topic of chemical research today. How to realize the efficient utilization of resources and develop new environmentally friendly green synthesis methods is one of the main directions of organic chemistry progress in the new century. Transition metal catalysis is a powerful method for constructing carbon-carbon bonds and carbon-heteroatom bonds, and has a wide range of applications in the fields of biology, medicine, and materials. [0003] Imidazopyridine compounds are an important class of biologically active compounds. The core s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 江焕峰高杨高颖兰伍婉卿彭建文
Owner SOUTH CHINA UNIV OF TECH
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