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Method for synthesizing pharmaceutical intermediate phenanthrene compound under a kind of diisopropylamine environment

A technology of diisopropylamine and compounds, which is applied in the fields of organic synthesis and pharmaceutical intermediate synthesis, can solve the problems of insufficient utilization of raw materials, low production efficiency, and failure to meet production needs, etc., and achieve a wide range of industrial application prospects and high yields Effect

Inactive Publication Date: 2018-08-14
嘉兴市金利化工有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] As mentioned above, although the preparation methods of various types of phenanthrene compounds have been disclosed in the prior art, these methods still cannot meet the production needs in the fields of medicine and chemical synthesis, because of their inherent low production efficiency and insufficient raw materials. Use and many other issues

Method used

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  • Method for synthesizing pharmaceutical intermediate phenanthrene compound under a kind of diisopropylamine environment
  • Method for synthesizing pharmaceutical intermediate phenanthrene compound under a kind of diisopropylamine environment
  • Method for synthesizing pharmaceutical intermediate phenanthrene compound under a kind of diisopropylamine environment

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Experimental program
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Effect test

Embodiment 1

[0047]

[0048] Add an appropriate amount of mixed solvent consisting of PEG-400 and 1-allyl-3-methylimidazolium tetrafluoroborate (the volume ratio of the two is 1:0.1) to the reactor, and then replace it twice with nitrogen, so that The reactor is a nitrogen atmosphere; then add 100mmol of the above formula (II) compound 2-bromo-4'-chlorobiphenyl, 200mmol of the above formula (III) compound styrene, by 3mmolPdCl 2 (dppf) and 6 mmol hexafluorophosphate tetraacetonitrile copper composite catalyst, 10 mmol ligand L1 and 200 mmol diisopropylethanolamine, heated to 60 ° C under stirring, and reacted at this temperature for 12 hours.

[0049] After the reaction, add deionized water to the reaction system, fully shake and wash, separate the organic layer, wash with deionized water again, separate the organic layer; concentrate the organic layer under reduced pressure, remove, and put the residue on a silica gel column Chromatography, eluting with a mixed solvent of n-hexanol and...

Embodiment 2

[0052]

[0053] Add an appropriate amount of mixed solvent (the volume ratio of the two is 1:0.2) consisting of PEG-400 and 1-allyl-3-methylimidazolium tetrafluoroborate to the reactor, and then replace it twice with nitrogen, so that The reactor is a nitrogen atmosphere; then add 100mmol of the formula (II) compound 2-bromobiphenyl, 300mmol of the formula (III) compound 1-methyl-3-vinylbenzene, by 3mmolPdCl 2 (dppf) and 9 mmol hexafluorophosphate tetraacetonitrile copper composite catalyst, 15 mmol ligand L1 and 250 mmol diisopropylethanolamine, heated to 70 ° C under stirring, and reacted at this temperature for 10 hours.

[0054] After the reaction, add deionized water to the reaction system, fully shake and wash, separate the organic layer, wash with deionized water again, separate the organic layer; concentrate the organic layer under reduced pressure, remove, and put the residue on a silica gel column Chromatography, eluting with a mixed solvent of n-hexanol and chlor...

Embodiment 3

[0057]

[0058] Add an appropriate amount of mixed solvent (the volume ratio of the two is 1:0.3) consisting of PEG-400 and 1-allyl-3-methylimidazolium tetrafluoroborate to the reactor, and then replace it twice with nitrogen, so that The reactor is a nitrogen atmosphere; then add 100mmol of the formula (II) compound 2-bromobiphenyl, 400mmol of the formula (III) compound 1-vinylnaphthalene, by 3mmolPdCl 2 (dppf) and 12 mmol hexafluorophosphate tetraacetonitrile copper composite catalyst, 20 mmol ligand L1 and 300 mmol diisopropylethanolamine, heated to 80 ° C under stirring, and reacted at this temperature for 8 hours.

[0059] After the reaction, add deionized water to the reaction system, fully shake and wash, separate the organic layer, wash with deionized water again, separate the organic layer; concentrate the organic layer under reduced pressure, remove, and put the residue on a silica gel column Chromatography, the mixed solvent of n-hexanol and chloroform with a vol...

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Abstract

The invention relates to a method for synthesizing a phenanthrene compound shown in the formula (I) in a diisopropylamine environment. The method comprises steps as follows: in the inert atmosphere, in the presence of a catalyst, organic ligands and diisopropylamine, a compound shown in the formula (II) and a compound shown in the formula (III) are subjected to a reaction in a solvent, and the compound shown in the formula (I) is obtained, wherein each of R1 and R2 independently represents H, C1-C6 alkyl, C1-C6 alkoxy or halogen; R3 represents C6-C10 aryl or C5-C8 heteroaryl, C6-C10 aryl or C4-C8 heteroaryl is substituted with 1-3 substituents, and the substituents are C1-C6 alkyl or halogen. The method has a good effect through selection of the proper catalyst, organic ligands, alkali and solvent and has wide industrial application prospect.

Description

[0001] The application of the present invention is a divisional application of the application number 201510100568.5 (a method for synthesizing pharmaceutical intermediate phenanthrene compounds) filed on March 6, 2015. technical field [0002] The invention relates to a method for synthesizing condensed ring compounds, more specifically to a method for synthesizing a pharmaceutical intermediate phenanthrene compound, and belongs to the fields of organic synthesis and pharmaceutical intermediate synthesis. Background technique [0003] Fused ring compounds such as naphthalene, anthracene, phenanthrene and other compounds have attracted the attention and attention of pharmaceutical researchers due to their ubiquitous biological activities. Among them, phenanthrene and its derivatives are an important class of aromatic compounds, which have been widely used in the fields of drug design and synthesis, and material research and development. [0004] It is precisely because of su...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C17/266C07C25/22C07D213/16C07D213/127C07C2/86C07C15/30
CPCC07C2/861C07C17/266C07D213/127C07D213/16C07C25/22C07C15/30
Inventor 翟学研
Owner 嘉兴市金利化工有限责任公司
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