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Synthetic C2-acetoxy-3-indolone compound and method

A kind of technology of acetoxy and compound, applied in the field of synthesizing C2-acetoxy-3-indolone compounds

Inactive Publication Date: 2017-01-04
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above-mentioned synthesis method requires the use of expensive noble metals as catalysts or complex ligands. Therefore, it is of positive significance to develop a simpler and more efficient reaction system to enrich and develop the reaction of constructing 3-indolinone compounds.

Method used

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  • Synthetic C2-acetoxy-3-indolone compound and method

Examples

Experimental program
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Effect test

experiment example 1

[0041] Synthesis of 3-oxo-2-acetoxy-1-(pyrimidin-2-yl)indole

[0042] In the reaction vessel, add indole (6mmol, 702.9mg), NaH (mass fraction 60%, 10.8mmol, 432mg), DMF solvent, and react under low temperature for 30 minutes; then add 2-chloropyrimidine (9.6mmol, 1099.488mg ), the mixture was reacted at 130° C. for 24 hours, cooled to room temperature, extracted to remove the solvent, and separated by column to obtain compound 1-(pyrimidinyl-2-yl)-1H-indole reactant. Accurately weigh the 1-(pyrimidinyl-2-yl)-1H-indole reactant (0.3mmol, 58.50mg) with an electronic balance of 1 / 10,000th, transfer to the thick-walled pressure-resistant tube of the reaction vessel, and add PhI to the reaction vessel (OAc) 2 (3eq, 289.5mg) was added dropwise 2mL of acetic acid / acetic anhydride = 7 / 3 mixed solvent, the reaction tube plug was tightened to seal the reaction system, heated to 60°C, and reacted for 36h under the condition of stirring in an oil bath. After the reaction was finished, t...

experiment example 2

[0045] Synthesis of 4-(Benzyloxy)-2-Acetoxy-3-oxo-1-(pyrimidin-2-yl)indole

[0046] Take a 100mL round bottom flask and a suitable size magnet, weigh 4-(benzyloxy)-1H-indole (5mmol, 1115mg) and dissolve it in N,N-dimethylformamide (DMF), and place Slowly add NaH (mass fraction 60%, 7.5mmol, 300mg) into an ice-water bath for hydrogen extraction reaction, transfer to an oil bath at 130°C after 1 hour of reaction, monitor the end of the reaction by TLC after 24 hours, dilute with ethyl acetate and transfer to A 250mL separatory funnel was washed three times with water. After washing the DMF, the organic phase was collected to remove water with anhydrous sodium sulfate, and the organic solvent was removed by rotary evaporation under reduced pressure to obtain a crude product, which was passed through column chromatography (ethyl acetate:petroleum ether= 3:95) to give the product 4-(benzyloxy)-1H-(pyrimidin-2-yl)-1H-indole reactant. Accurately weigh the 4-(benzyloxy)-1H-(pyrimidin...

experiment example 3

[0049] Synthesis of 5-methyl-2-acetoxy-3-oxo-1-(pyrimidin-2-yl)indole

[0050] Take a 100mL round bottom flask and a suitable size magnet, weigh 5-methyl-1H-indole (5mmol, 755mg) and dissolve it in N,N-dimethylformamide (DMF), and place it in an ice-water bath Slowly add NaH (mass fraction 60%, 7.5mmol, 300mg) for hydrogen extraction reaction, react for 1 hour, transfer to 130°C oil bath, monitor the end of the reaction by TLC after 26 hours, dilute with ethyl acetate and transfer to 250mL for liquid separation The funnel was washed three times with water, and after washing the DMF, the organic phase was collected to remove water with anhydrous sodium sulfate, and the organic solvent was removed by rotary evaporation under reduced pressure to obtain a crude product, which was obtained by column chromatography (ethyl acetate:petroleum ether=2:95 ) to give the product 5-methyl-1H-(pyrimidin-2-yl)-1H-indole reactant. Accurately weigh the 5-methyl-1H-(pyrimidin-2-yl)-1H-indole re...

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Abstract

The invention discloses a synthetic C2-acetoxy-3-indolone compound and a method thereof. The method comprises the following steps: using indole compounds as raw materials; carrying out a reaction between indole or substituent indole with 2-chloropyrimidine under alkaline conditions of sodium hydride to generate 1-(pyrimidinyl-2-yl)-1H-indole compound; introducing a pyrimidine directing group into the indole compound; allowing 1-(pyrimidinyl-2-yl)-1H-indole compound to participate in an oxidation reaction in the presence of iodosobenzene diacetate as an oxidant and a mixed solvent of acetic acid and acetic anhydride; finally synthesizing the C2-acetoxy-3-indolone compound. As an indole structure is directly used in an oxidizing reaction, a pre-functionalization process is eliminated to reduce reaction steps, the reaction economic efficiency is improved, and the C2-acetoxy-3-indolone compound is synthesized effectively under a relatively mild condition. The structural unit can be used as pharmaceutical intermediate, polymer substrate, premise of total synthesis, and has a wide biological activity and a broad application prospect.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis chemistry, and specifically relates to a method for synthesizing C2-acetoxy-3-indolinone compounds. Background technique [0002] 3-indolinone homologues or derivatives are important heterocyclic compounds. The 3-indolinone structure exists in many pharmaceutically active molecules and is widely used in the fields of material chemistry and medicinal chemistry. [0003] Conventional non-indole direct oxidation synthesis of 3-indolinones can be divided into two categories: [0004] One is the ring-forming reaction, generally the ring-forming reaction of 1-nitro-2-(phenylethynyl) benzene analogues or the reaction of N-(2-ethynylphenyl)-4-methylbenzenesulfonamide analogues ring-forming reaction. Raw materials for such reactions are not easy to obtain, and some reactions require noble metals or various complex ligands. For example, in 2011, the Gagosz research group used 1-azido-2-(but-1-y...

Claims

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Application Information

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IPC IPC(8): C07D403/04
CPCC07D403/04
Inventor 姜超杨超
Owner NANJING UNIV OF SCI & TECH
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