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Synthetic method for 3,3-difluoro-2-oxindole derivative

A technology for indole derivatives and synthesis methods, which is applied in the field of synthesis of 3,3-difluoro-2-oxindole derivatives, can solve problems such as increased synthesis costs and drug research and development costs, and achieves reduction in usage, The effect of safe use and low reaction temperature

Inactive Publication Date: 2016-03-02
HENAN INST OF ENG
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The reason is that the use of metals often doubles the cost of synthesis. In addition, the participation of trace amounts of metals also increases the obstacles to the application of drugs. In order to remove these traces of residual metals, further processing methods are needed, which often It also greatly increases the cost of drug development

Method used

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  • Synthetic method for 3,3-difluoro-2-oxindole derivative
  • Synthetic method for 3,3-difluoro-2-oxindole derivative
  • Synthetic method for 3,3-difluoro-2-oxindole derivative

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Experimental program
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Embodiment 1

[0027] Target product I-1 is The synthesis steps are as follows:

[0028] 1. Synthesis of Aromatic Amides

[0029]Weigh 1.23g (10mmol) of p-methoxyaniline and add it to a 100mL single-necked round-bottomed flask, add 1.92mL (15mmol) of ethyl difluorobromoacetate respectively, put in a magnet, and under nitrogen protection, at 25°C Stir for 6 hours, stop stirring; add 30mL water and 50mL ethyl acetate to the flask, stir for another 5 minutes, transfer the solution to a separatory funnel, and the solution is separated after the reaction; The ester layer was washed once with dilute hydrochloric acid aqueous solution (0.5mol / L) and once with saturated brine; dried over anhydrous sodium sulfate, and evaporated the solvent under reduced pressure at 45°C to obtain light yellow powder 2-bromo-2,2-di Fluoro-N-(4-methoxyphenyl)acetamide 2.72 g (97% yield).

[0030]

[0031] 2. Synthesis of N-alkyl protected aromatic amides:

[0032] 1.4g (5mmol) of 2-bromo-2,2-difluoro-N-(4-meth...

Embodiment 2

[0038] Target product I-2 is The only difference between the synthesis steps and Example 1 is that p-methylaniline is used instead of p-methoxyaniline.

Embodiment 3

[0040] Target product I-3 is The only difference between the synthetic steps and Example 1 is that p-methoxyaniline is replaced by aniline.

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Abstract

The present invention belongs to the technical field of pharmaceutical chemical synthesis, and specifically discloses a synthetic method for a 3,3-difluoro-2-oxindole derivative. The method comprises: selecting different aromatic amines and esters of bromoacetic acid fluoride to generate an aromatic amide compound; carrying out a reflux reaction on halohydrocarbon and the aromatic amide compound to obtain the (N)-alkyl protected aromatic amide compound; and adding an accelerant and an organic solvent into the obtained (N)-alkyl protected aromatic amide compound at the temperature of 50-100 DEG C to react for 6-10 hours, and synthesizing the 3,3-difluoro-2-oxindole derivative. According to the synthetic method disclosed by the present invention, the synthetic method is simple to operate without using any metals, the cost is very low, the condition is mild, the conversion rate is high, and the used raw materials are readily available and inexpensive, so that the synthetic method is suitable for being applied to industrial production.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical chemical synthesis, and in particular relates to a synthesis method of 3,3-difluoro-2-oxindole derivatives. Background technique [0002] At present, the synthesis of fluorine-containing compounds and the research on their methodology have become a hot spot and focus in organic synthesis, especially in drug development, because small organic molecules can improve their lipophilicity after being connected with fluorine atoms. If it is used as a drug, it can improve its metabolic stability and biocompatibility; in terms of materials science, the introduction of fluorine atoms can also change the characteristics of the material and make it have unique properties, such as the gas permeability of the material. [0003] Derivatives of oxindole are widely found in natural products and biologically active substances, such as indigo, which was used as a dye in the early stage, contains the structure...

Claims

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Application Information

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IPC IPC(8): C07D209/34
CPCC07D209/34
Inventor 买文鹏吕名秀杨柳曹毅王延伟卢奎
Owner HENAN INST OF ENG
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