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Preparation method of 3-(2-methylindolyl-3-)pyrryl-2,5-dione

A technology of methyl indole and diketone, which is applied in the field of preparation of pharmaceutical synthesis intermediates, can solve the problems of long reaction time, long reaction route and high cost, and achieves the effects of short reaction route, low cost and reduction of three-waste treatment.

Inactive Publication Date: 2013-02-27
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, recently, Zhao Shengyin et al. also reported the use of zinc bromide as a catalyst to prepare indole-3-succinimide compounds (Zhao Shengyin, An Yulong. A method for preparing indole-3-succinimide, CN102702175) , but when this type of catalyst reacts with 2-methylindole and succinimide as raw materials, the reaction is slow and the reaction time is long. In summary, the above-mentioned method has long reaction route, low yield and long reaction time, etc. Disadvantage, relatively high cost in mass production

Method used

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  • Preparation method of 3-(2-methylindolyl-3-)pyrryl-2,5-dione

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Experimental program
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Effect test

Embodiment 1

[0030] Take 26.2g (0.2mol) of 2-methylindole, 19.4g (0.2mol) of maleimide and 5.0mL (0.04mol) of boron trifluoride ether into a 500mL round bottom flask, add 1,2- Dichloroethane 300mL, stirred and refluxed for 5h, after the reaction was completed, distilled and recovered 1,2-dichloroethane, added 300mL of water, stirred for 10 minutes, suction filtered, washed with water, and the obtained solid was recrystallized with 95% ethanol to obtain a white solid 39.7 g, yield 87%, mp: 198~200°C.

Embodiment 2

[0032] Take 26.2g (0.2mol) of 2-methylindole, 19.4g (0.2mol) of maleimide and 5.0mL (0.04mol) of boron trifluoride ether and add them to a 500mL round bottom flask, add 300mL of chloroform, and heat Stir and reflux the reaction for 24 hours. After the reaction is complete, distill off the chloroform and recover it. Add 300 mL of water, stir for 35 minutes, filter with suction, wash with water, and recrystallize the obtained solid with 95% ethanol to obtain 34.7 g of white solid, yield 76%, mp: 197~200 ℃.

Embodiment 3

[0034] Take 26.2g (0.2mol) of 2-methindole, 19.4g (0.2mol) of maleimide and 5.0mL (0.04mol) of boron trifluoride ether into a 500mL round bottom flask, add 1,2-di Add 300 mL of ethyl chloride, heat to 70°C and stir for 14 hours. After the reaction is complete, distill and recover 1,2-dichloroethane, add 300 mL of water, stir for 60 minutes, filter with suction, and wash with water. The obtained solid was recrystallized with 95% ethanol to obtain 33.3 g of white solid, yield 73%, mp: 196~199°C.

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Abstract

The invention relates to a preparation method of 3-(2-methylindolyl-3-)pyrryl-2,5-dione, which comprises the following steps: (1) adding 2-methylindole, maleimide and Lewis acid in a mol ratio of 1.0:(1.0-1.5):(0.2-1.0) into reaction solvent, and reacting under reflux at room temperature to 100 DEG C for 5-24 hours, thereby obtaining a yellow white solution; and (2) evaporating to remove the solvent, adding water, stirring, carrying out vacuum filtration, and recrystallizing the obtained solid with ethanol to obtain the 3-(2-methylindolyl-3-)pyrryl-2,5-dione. In the process of preparing the 3-(2-methylindolyl-3-)pyrryl-2,5-dione, by using boron trifluoride and other Lewis acid as a catalyst, the reaction time is shortened, and the treatment of three wastes is lowered. The method has the advantages of higher yield, accessible raw materials, low cost, simple reaction operation and short reaction route, can easily implement industrial production, and has wide favorable application prospects.

Description

technical field [0001] The invention belongs to the field of preparation of pharmaceutical synthesis intermediates, in particular to a preparation method of 3-(2-methylindole-3-)pyrrole-2,5-dione. Background technique [0002] 3-(2-methylindole-3-)pyrrole-2,5-dione and its derivatives are important drug synthesis intermediates, which can be used to synthesize sirtuin inhibitor antitumor drugs ( Brooks, Clinton A.; Chen, Christine Hiu-Tung; Cho, Young Shin; Jiang, Lei; Liu, Gang; Shultz, Michael US20110060009; Cho, Young Shin; Whitehead, Lewis; Li, Jianke; Chen, Christine H.- T.; Jiang, Lei; Vogtle, Markus; Francotte, Eric; Richert, Paul; Wagner, Trixie; Traebert, Martin; Lu, Qiang; Cao, Xueying; ; Yan-Neale, Yan; Shao, Wenlin; Atadja, Peter; Shultz, Michael. Journal of Medicinal Chemistry, 2010, 53(7):2952-2963). According to literature reports, the synthesis method of 3-(2-methylindole-3-)pyrrole-2,5-dione mainly uses 2-methylindole and maleimide as raw materials, and ref...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/04
Inventor 赵圣印安玉龙
Owner DONGHUA UNIV
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