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A kind of preparation method of 3-substituted-3-azidoindol-2-one compound

A technology for ketone compounds and azidoindole, which is applied in the field of preparation of 3-substituted-3-azidoindole-2-one compounds, can solve the problem of low reaction yield and narrow application range of reaction substrates , long response time, etc.

Active Publication Date: 2021-04-20
NINGBO UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method still has disadvantages such as long reaction time, narrow application range of reaction substrates, and low reaction yield when CuBr is used as a catalyst.
[0004] Although the prior art has reported a variety of methods for the synthesis of 3-substituted-3-azidolindol-2-ones represented by the above, it is easy to explore under green, mild and efficient conditions. Synthetic strategies to prepare 3-substituted-3-azidolindol-2-ones remain desirable and challenging

Method used

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  • A kind of preparation method of 3-substituted-3-azidoindol-2-one compound
  • A kind of preparation method of 3-substituted-3-azidoindol-2-one compound
  • A kind of preparation method of 3-substituted-3-azidoindol-2-one compound

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Experimental program
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Effect test

Embodiment 14

[0039] Embodiment 14 uses sodium azide as the azide source compound

[0040]

[0041] Add a magnetic stirring bar in the Schlenk lock reactor, add the sodium azide (0.4mmol) shown in 3-phenylindol-2-ketone (0.2mmol) shown in II-1 and formula III-2 ), then add PhI(OAc) 2 (0.4 mmol), triethylamine (0.4 mmol) and MeCN (2 mL). Then, the reactor was placed at room temperature (25° C.) and stirred for 2 hours, and the reaction was complete as monitored by TLC. The reaction solution was concentrated under reduced pressure, and the residue was separated by silica gel column chromatography (using n-hexane / ethyl acetate as eluent) to obtain the target product I-1 with a yield of 56%.

Embodiment 15

[0043] Using benzenesulfonyl azide as the azide source, the rest of the operations were the same as in Example 14, and the yield of the target product I-1 was 18%.

Embodiment 16

[0045] Using p-toluenesulfonyl azide as the azide source, the rest of the operations were the same as in Example 14, and the yield of the target product I-1 was 12%.

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Abstract

The application belongs to the field of organic synthesis methodology, and specifically relates to a preparation method of 3-substituted-3-azidoindol-2-ketone compounds. The object of the present invention is to provide a synthetic method for the preparation of 3-substituted-3-azidoindole-2-ketones with simple process, green and high-efficiency, and mild conditions. The method uses 3-substituted indole-2- Ketones are used as raw materials, in oxidants, reaction aids and organic solvents, react with azide sources at room temperature, and are conveniently prepared with excellent yields to obtain 3-substituted-3-azidoindole-2- Ketones.

Description

technical field [0001] The application belongs to the field of organic synthesis methodology, and in particular relates to a preparation method of 3-substituted-3-azidoindol-2-one compounds. Background technique [0002] 3-Substituted-3-azidoindol-2-one compounds are important drug synthesis intermediates (see CN103443076, US5594023). The synthetic method of prior art usually needs to obtain corresponding 3-halogenated raw material earlier, on this basis, reacts with azide compound, and then prepares and obtains 3-azidoindol-2-one (3.J.Org.Chem .1991, 56, 3637-3642; 4.Terrahedron 1992, 48, 5359-5374.), or with 3-oxindoledione as raw material, in Ga(OTf) 3 Obtained by reaction under catalytic conditions (5. Acta Chim. Sinica 2015, 73, 685-689), such a method has a longer reaction process and lower reaction efficiency. Other synthetic methods require specific and expensive azide reagents (6.Org.Lett.2014, 16, 2302-2305), or carry out under the expensive transition metal cata...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/40
CPCC07D209/40
Inventor 高乐涵魏文廷徐旭东
Owner NINGBO UNIV