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Method for preparing substituted 2-indolinone compound

A technology of ketone compounds and indole, which is applied in the field of preparation of substituted indol-2-one compounds, can solve the problems of high reaction temperature, low reaction yield, and difficulty in obtaining it, and achieve convenient and simple post-processing Convenience and mild reaction conditions

Inactive Publication Date: 2012-05-02
SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The above two methods all have defects such as expensive raw materials or catalysts and not easy to obtain to a certain extent.
[0009] 3. Wilk, Crestini and others found that using hydrazine hydrate as a reducing agent can reduce isatin derivatives to indol-2-one compounds (Organic Preparations and Procedures International 2005, 37(3), 283-285). The advantage of the method is that the raw material is cheap and easy to obtain; the disadvantage is that the highly toxic hydrazine hydrate needs to be used as a reducing agent in the reaction, the reaction temperature is high (120 ° C), the post-treatment and product separation and purification are difficult, and the reaction yield is not high. Only about 70%, and the appearance color of the product is not ideal

Method used

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  • Method for preparing substituted 2-indolinone compound
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  • Method for preparing substituted 2-indolinone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment one: the preparation of 5-bromoindol-2-one:

[0024] Under the protection of nitrogen, add 100ml trifluoroacetic acid and 34.8g (0.3mol) triethylsilane in the 250ml reaction bottle, after stirring evenly, add 22.6g (0.1mol) 5-bromoisatin in batches at room temperature, after adding The reaction was stirred for 12 hr at room temperature. Concentrate under reduced pressure to remove trifluoroacetic acid, then add 50ml of diethyl ether, stir for 1 hr, filter, wash with diethyl ether, and drain to obtain an off-white solid. After drying, 19.5g of 5-bromoindol-2-one is obtained, with a yield of 91.9%, mp =217~219°C, -cESI=212.05, 1HNMR-δ((CD 3 ) 2 SO) / 300MHz): 10.38(s, 1H), 7.44-7.31(m, 2H), 6.74(d, J=8.0Hz, 1H), 6.27(d, J=7.7Hz, 1H), 4.86(d, J=7.6Hz, 1H).

Embodiment 2

[0025] Example 2: Preparation of 5-fluoroindol-2-one:

[0026] Take 16.5g (0.1mol) of 5-fluoroisatin and prepare according to the method of Example 1 to obtain 13.6g of 5-fluoroindol-2-one, the yield is 90.3%, mp=141~143°C, -cESI=150.08, 1H NMR-δ((CD 3)2 SO) / 300MHz): 10.25(s, 1H), 7.12(dd, J=8.1, 2.5Hz, 1H), 7.08-6.96(m, 1H), 6.76(dd, J=8.4, 4.3Hz, 1H), 6.26 (d, J=7.6Hz, 1H), 4.84 (d, J=7.6Hz, 1H).

Embodiment 3

[0027] Embodiment three: the preparation of 5-chloroindol-2-one:

[0028] Take 18.2g (0.1mol) of 5-chloroisatin and prepare it according to the method of Example 1 to obtain 15.6g of 5-chloroindol-2-one, the yield is 92.7%, mp=196~198°C, -cESI=166.87, 1H NMR-δ((CD 3)2 SO) / 300MHz): 10.35(s, 1H), 7.30-7.21(m, 2H), 6.77(dd, J=8.1, 4.9Hz, 1H), 6.27(d, J=7.6Hz, 1H), 4.86( d, J=7.6Hz, 1H).

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Abstract

The invention relates to a method for preparing a substituted 2-indolinone compound, which comprises the following steps of: reducing a substituted isatin compound by triethyl silicane / trifluoroacetic acid; concentrating; and filtering after washing by using an organic solvent so as to obtain the target substituted 2-indolinone compound. In the method, various substituted isatins with wide sources and low price are used as the raw materials; the reaction condition is mild; the substituted 2-indolinone compound is prepared under high yield; and the method has the advantage of convenience and simpleness in posttreatment.

Description

Technical field: [0001] The invention relates to a chemical synthesis method of various substituted indol-2-one compounds, which has the advantages of mild reaction conditions, high yield, convenient and simple post-treatment, and the like. Background technique: [0002] Substituted indol-2-one compounds are important intermediates of some drugs and pesticides, and have been widely used in the fields of tyrosine kinase receptor inhibitors and photokinase inhibitors, such as Sunitibib, Hesperadin, etc., and their structural formula is as follows: [0003] [0004] The synthetic method of this class compound mainly contains: 1, take substituted indole as raw material, assist with chloride peroxidase catalysis, obtain the method (Catal Lett 2009,129 , 457-461). The synthetic route is: [0005] [0006] 2. Using o-aminophenylacetic acid ester derivatives as starting materials, catalyzed by molecular sieves to cyclize them into indol-2-one compounds (ORGANIC LETTERS 2009,...

Claims

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Application Information

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IPC IPC(8): C07D209/34
Inventor 周有骏周峰朱驹吕加国郑灿辉刘嘉刘娜任晓慧李维张猛
Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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