Catalytic synthesis method of 6-difluorophenanthridine compound

A synthetic method, the technology of diflurphenidine, which is applied in the field of catalytic synthesis, can solve problems that have not been reported before, achieve good functional group compatibility, simple operation, and improve the effect of application prospects

Active Publication Date: 2018-10-19
HUAQIAO UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, despite great developments in the difluoroalkylation and difluoromethylation of difluoro compounds, the method of cutting four bonds of a carbon atom to form a new source of C has not been reported so far.
There are several unprecedented challenges: (1) how to cut four different bonds in one step reaction, which also includes two stable C-F bonds on the same carbon atom (2) how to use in situ generation of C1, converting it into valuable products

Method used

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  • Catalytic synthesis method of 6-difluorophenanthridine compound
  • Catalytic synthesis method of 6-difluorophenanthridine compound
  • Catalytic synthesis method of 6-difluorophenanthridine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] The reaction formula of this embodiment is as follows:

[0021]

[0022] (1) 0.2mmol o-aminobiphenyl, 0.6mmol ethyl bromodifluoroacetate, 0.02mmol Cu(OTf) 2 , 0.024mmol 1,10-phenanthroline, 0.6mmol sodium carbonate, and 2mL acetonitrile were placed in a pressure-resistant sealed reaction tube, filled with nitrogen and stirred in an oil bath at 120°C for reaction, followed by TLC and GC during the reaction To determine the specific reaction time, the reaction time is 20h;

[0023] (2) Cool the material obtained in step (1) to room temperature, add ethyl acetate to fully mix, filter, then wash with ethyl acetate, and finally combine the organic phases;

[0024] (3) spin dry the solvent in the organic phase of step (2) gained, rear use silica gel column purification product, then obtain described 1,6-difluoroacetate ethyl phenanthridine with eluent rinse, productive rate is 82 %, the eluent is a mixed solution of petroleum ether and ethyl acetate, and the volume ratio...

Embodiment 2

[0026] (1) 0.2mmol o-aminobiphenyl compounds, 0.6mmol ethyl bromodifluoroacetate, 0.02mmol Cu(OTf) 2 , 0.024mmol 1,10-phenanthroline, 0.6mmol sodium carbonate, and 2mL acetonitrile were placed in a pressure-resistant sealed reaction tube, filled with nitrogen and stirred in an oil bath at 120°C for reaction, followed by TLC and GC during the reaction To determine the specific reaction time, the reaction time is 20h;

[0027] The above-mentioned o-aminobiphenyl compounds are at least one of the following:

[0028]

[0029] (2) Cool the material obtained in step (1) to room temperature, add ethyl acetate to fully mix, filter, then wash with ethyl acetate, and finally combine the organic phases;

[0030] (3) spin dry the solvent in the organic phase of step (2) gained, after using silica gel column purification product, then obtain described 6-difluorophenanthidine compound with eluent rinse, this eluent is sherwood oil and ethyl acetate, and the volume ratio of petroleum et...

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PUM

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Abstract

The invention discloses a catalytic synthesis method of a 6-difluorophenanthridine compound. According to the catalytic synthesis method disclosed by the invention, an o-aminobiphenyl compound and ethyl bromodifluoroacetate are subjected to defluorination reaction under the participation of Cu(OTf)2, so as to obtain the 6-difluorophenanthridine compound. The reaction has good functional group compatibility; drugs used by the catalytic synthesis method provided by the invention can be directly purchased and the catalytic synthesis method is simple to operate and has high efficiency and safety;the reaction is simple and an application prospect of the reaction in industry is greatly improved.

Description

technical field [0001] The invention belongs to the technical field of catalytic synthesis, and in particular relates to a method for catalytic synthesis of 6-difluorophenanthidine compounds. Background technique [0002] Halogenated difluoromethyl compounds are widely used as a fluorine reagent and difluorocarbene. Many methods use difluoroalkylation and difluoromethylation to break a C-Br bond or break two C-Br bonds. Br and C-COOM fracture. However, despite great developments in the difluoroalkylation and difluoromethylation of difluoro compounds, the method of cutting four bonds of a carbon atom to form a new source of C has not been reported so far. There are several unprecedented challenges: (1) how to cut four different bonds in one step reaction, which also includes two stable C-F bonds on the same carbon atom (2) how to use in situ generation of C1, transforming it into valuable products. Contents of the invention [0003] The purpose of the present invention i...

Claims

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Application Information

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IPC IPC(8): C07D221/12C07D491/056C07D221/18C07D471/04C07D487/04
CPCC07D221/12C07D221/18C07D471/04C07D487/04C07D491/056
Inventor 宋秋玲马星星
Owner HUAQIAO UNIVERSITY
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