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A method of applying pdcl2(pph3)2 to synthesize pharmaceutical intermediate phenanthrene compound

A compound and catalyst technology, which is applied in the synthesis of pharmaceutical intermediates, phenanthrene compounds, and the synthesis of condensed ring compounds, can solve the problems of insufficient utilization of raw materials, low production efficiency, and inability to meet production needs, and achieve broad industrial application prospects and high yields. rate effect

Active Publication Date: 2018-08-24
威海区域创新中心有限责任公司
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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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  • A method of applying pdcl2(pph3)2 to synthesize pharmaceutical intermediate phenanthrene compound
  • A method of applying pdcl2(pph3)2 to synthesize pharmaceutical intermediate phenanthrene compound
  • A method of applying pdcl2(pph3)2 to synthesize pharmaceutical intermediate phenanthrene compound

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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 6mmol tetraacetonitrile copper hexafluorophosphate composite catalyst, 10mmol ligand L1 and 200mmol 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 chlo...

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 as shown in a formula (I) (Please see the formula (I) in the description.) by means of PdCl2(PPh3)2.The method comprises the steps that a compound as shown in a formula (II) reacts with a compound as shown in a formula (III) (Please see the formula (II) and the formula (III) in the description.) in an inert atmosphere in the presence of a catalyst containing PdCl2(PPh3)2, organic ligands and alkali in a solvent, and the compound as shown in the formula (I) is obtained, wherein R1 and R2 are independently selected from H or C1-C6 alkyl or C1-C6 alkoxy or halogens, R3 is C6-C10 aryl or C5-C8 ceteroary, the C6-C10 aryl or C5-C8 ceteroary is optionally substituted with 1-3 substitutional groups, and the substitutional groups are C1-C6 alkyl or the halogens.According to the method, by means of selection of the proper catalyst, organic ligands, alkali and solvent, a good effect is achieved, and the method has a 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): C07B37/10C07C25/22C07C17/266C07C15/30C07C2/86C07D213/127C07D213/16
CPCC07B37/10C07C2/861C07C17/266C07D213/127C07D213/16C07C25/22C07C15/30
Inventor 翟学研
Owner 威海区域创新中心有限责任公司
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