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A kind of synthetic method of indolinone compound

A synthetic method and compound technology, applied in the direction of organic chemistry, can solve the problems of insufficient sources and expensive prices, and achieve the effect of broad market prospects and good reaction effects

Active Publication Date: 2017-11-10
烟台坤益液晶显示材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the fluorination reagents used in the prior art are relatively expensive, and the sources are not wide enough, and rare precious metal catalysts are often used

Method used

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  • A kind of synthetic method of indolinone compound
  • A kind of synthetic method of indolinone compound
  • A kind of synthetic method of indolinone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033]

[0034] At room temperature, add 100mmol of the above formula (I) compound, 160mmol of the above formula (II) compound, 6mmol of the catalyst (a mixture of 3mmol of ceric ammonium nitrate and 3mmol of silver trifluoroacetate), and 140mmol of the initiator in an appropriate amount of organic solvent PEG-200. Azobisisoheptanonitrile, 50mmol base DMEDA and 21mmol auxiliary agent (a mixture of 7mmol N-fluorobisbenzenesulfonamide (NFSI) and 14mmol 2-iodoethyl methyl ether), then stirred at 70°C for 8 Hour.

[0035] After the reaction, filter, add an equal volume of diethyl ether and water mixture to the filtrate, shake fully, then stand still, separate the organic phase, and dry it with anhydrous magnesium sulfate, remove the solvent by rotary evaporation, and pass the residue through a 200-300 mesh silica gel column Chromatography, using a mixture of acetone and petroleum ether at a volume ratio of 1:2 as the eluent, thereby obtaining the compound of the above formula (...

Embodiment 2

[0039]

[0040] At room temperature, add 100mmol of the above formula (I) compound, 180mmol of the above formula (II) compound, 9mmol of the catalyst (a mixture of 3mmol of ceric ammonium nitrate and 6mmol of silver trifluoroacetate), and 160mmol of the initiator in an appropriate amount of organic solvent PEG-200. Azobisisoheptanonitrile, 70mmol base DMEDA and 30mmol auxiliary agent (a mixture of 10mmol N-fluorobisbenzenesulfonamide (NFSI) and 20mmol 2-iodoethyl methyl ether), then stirred at 80°C for reaction 6 Hour.

[0041] After the reaction, filter, add an equal volume of diethyl ether and water mixture to the filtrate, shake fully, then stand still, separate the organic phase, and dry it with anhydrous magnesium sulfate, remove the solvent by rotary evaporation, and pass the residue through a 200-300 mesh silica gel column Chromatography, using a mixture of acetone and petroleum ether at a volume ratio of 1:2 as the eluent, thereby obtaining the compound of the above...

Embodiment 3

[0045]

[0046] At room temperature, add 100mmol of the above formula (I) compound, 200mmol of the above formula (II) compound, 12mmol of the catalyst (a mixture of 5mmol of ceric ammonium nitrate and 7mmol of silver trifluoroacetate), and 180mmol of the initiator in an appropriate amount of organic solvent PEG-200. Azobisisoheptanonitrile, 80mmol base DMEDA and 39mmol auxiliary agent (a mixture of 13mmol N-fluorobisbenzenesulfonamide (NFSI) and 26mmol 2-iodoethyl methyl ether), then stirred at 90°C for 5 Hour.

[0047] After the reaction, filter, add an equal volume of diethyl ether and water mixture to the filtrate, shake fully, then stand still, separate the organic phase, and dry it with anhydrous magnesium sulfate, remove the solvent by rotary evaporation, and pass the residue through a 200-300 mesh silica gel column Chromatography, using a mixture of acetone and petroleum ether at a volume ratio of 1:2 as the eluent, thereby obtaining the compound of the above formula...

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Abstract

The invention provides an indolone compound synthesis method. The structural formula of an indolone compound is as shown in (III). The method includes the steps that under the room temperature, a compound as shown in (I), a compound as shown in (II), a catalyst, an initiator, alkali and an additive are sequentially added to an organic solvent, then the mixture is stirred at the temperature of 70 DEG C to 90 DEG C for 5-8 hours, post-processing is conducted after the reaction is completed, and thus the compound as shown in (III) is obtained, wherein R1 is selected from H or C1-C6 alkyl groups, R2 is selected from H or C1-C6 alkyl groups, R3 is selected from C1-C6 alkyl groups, and Rf is C1-8 perfluoroalkyl groups. According to the method, by selecting the catalyst, the initiator, the alkali, the additive and the organic solvent appropriately, the reaction system has the good reaction effect, the yield of target products is high, the industrial production requirement is met, and the method has wide market prospects.

Description

technical field [0001] The present invention relates to a method for synthesizing indole compounds, more particularly to a method for synthesizing indolone compounds, belonging to the field of organic synthesis, especially the field of pharmaceutical intermediate synthesis. Background technique [0002] Indolinone is a nitrogen-containing aromatic heterocyclic compound, which exists in various natural compounds or pharmaceutical compounds. In order to continue modification or follow-up reactions, introducing fluorinated groups is a common method for constructing new drugs and reagents, such as using Togni reagents, TMSCF 3 、CF 3 SO 2 The modification of fluorinated groups by Na et al. has attracted the interest of many researchers. [0003] Because of this, the fluorination modification method of indolinone compounds has attracted more and more attention. [0004] At present, a variety of synthetic methods of indolinone compounds have been developed in the prior art, as ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/34
CPCC07D209/34
Inventor 崔文娟李淑青刘清茂
Owner 烟台坤益液晶显示材料有限公司