Synthesis method of 3,3'-disubstituted-2-indolone compound

A synthesis method and compound technology, applied in 3 fields, can solve the problems of complex synthesis process steps and high cost, and achieve the effects of wide adaptability, low price and high yield

Active Publication Date: 2019-07-02
NANCHANG HANGKONG UNIVERSITY
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  • Claims
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Problems solved by technology

[0005] The purpose of the present invention is to overcome the defects of complicated synthetic process steps and high cost in the preparation of 3,3'-disubstituted-2-indolone compounds in the prior art, and to provide a method for preparing 3,3'-disubstituted-2- A new method for indolinone compounds. The method uses aniline compounds as raw materials and reacts with ethyl bromoacetate compounds to directly prepare 3,3'-disubstituted-2-indolinone compounds, which is economical, convenient, The advantages of easy-to-obtain raw material sources, low-cost catalytic system, wide application range of reaction substrates, and high yield of target products

Method used

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  • Synthesis method of 3,3'-disubstituted-2-indolone compound
  • Synthesis method of 3,3'-disubstituted-2-indolone compound
  • Synthesis method of 3,3'-disubstituted-2-indolone compound

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Experimental program
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Embodiment 1-20

[0030] Embodiment 1-20 reaction condition optimization test

[0031] With di-p-tolylamine shown in formula II-1 and 2-bromo-2-methylpropionate raw materials shown in formula III-1, the influence of different reaction conditions on the process optimization results was discussed, and the Representative examples 1-20, the results are shown in Table 1:

[0032]

[0033] Wherein, the test operation of embodiment 1 is as follows:

[0034] In the dry, airtight 25mL Schlenk sealed tube reactor, add the xylamine (0.3mmol) shown in the formula II-1, the 2-bromo-2-methylpropionic acid ethyl alcohol shown in the formula III-1 successively Esters (2equiv, 0.6mmol), Cu(OAc) 2 (10mol%), 2,2'-bipyridine (20mol%), K 2 CO 3 (2equiv, 0.6mmol), followed by adding the solvent acetonitrile (2mL), and reacting at 120°C for 12h. After the reaction was complete, the reaction solution was concentrated in vacuo, and the residue was separated by silica gel column chromatography (n-hexane / ethyl ac...

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Abstract

The invention discloses a synthesis method of a 3,3'-disubstituted-2-indolone compound. The synthesis method comprises the following steps: with an aniline compound as a raw material, directly carrying out a reaction with ethyl bromoacetate compound for obtaining the 3,3'-disubstituted-2-indolone compound. The method has the advantages of economy, convenience, easily available raw material sources, wide reaction substrate application range and high target product yield.

Description

technical field [0001] The application belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of 3,3'-disubstituted-2-indolinone compounds. Background technique [0002] 2-Indolinone, also known as oxindole, is an aromatic heterocyclic compound and the parent structure of many natural alkaloids and synthetic drugs. It is also a very important lead compound for drug design and an intermediate in organic synthesis. body. According to existing research in this field, the development and application of drugs based on 2-indolinone derivatives have made great progress in recent decades, among which 2-indolinone approved by the US FDA for disease treatment Such drugs include Sunitinib, Nintedanib, Ropinirole, Flindokalner, Tenidap, XEN402, Ziprasidone, Satavaptan, Simazani, etc. The 2-indolinone compounds that are undergoing or have completed clinical trials include TSU-68 (Orantinib), BIBF-1000, PHA-665752, GW5074, NS309, etc. (see 1...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/34C07D209/60C07D209/96C07D209/42C07D491/056
CPCC07D209/34C07D209/60C07D209/96C07D209/42C07D491/056
Inventor 宋仁杰曹安主李金恒
Owner NANCHANG HANGKONG UNIVERSITY
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