Method for synthesizing medical intermediate phenanthrene compound

A synthesis method and compound technology, which are applied in the synthesis of fused ring compounds and the synthesis of pharmaceutical intermediates phenanthrene compounds, can solve problems such as low production efficiency, insufficient utilization of raw materials, and inability to meet production requirements, and achieve high yield and wide The effect of industrial application prospects

Active Publication Date: 2015-06-10
NANTONG YOUYUAN ART PATTERN DESIGN CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] 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. Make full use of and many other issues

Method used

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  • Method for synthesizing medical intermediate phenanthrene compound
  • Method for synthesizing medical intermediate phenanthrene compound
  • Method for synthesizing medical intermediate phenanthrene compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046]

[0047] 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 3mmol PdCl 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.

[0048] 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 an...

Embodiment 2

[0051]

[0052] 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 formula (II) compound 2-bromobiphenyl, 300mmol of formula (III) compound 1-methyl-3-vinylbenzene, 3mmol PdCl 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.

[0053] 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 chloroform with...

Embodiment 3

[0056]

[0057] 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 3mmol PdCl 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.

[0058] 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 vo...

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Abstract

The invention relates to a method for synthesizing a phenanthrene compound shown as a formula (I). The structural formula is as shown in the specification. The method comprises the following steps: enabling a compound shown as a formula (II) to react with a compound shown as a formula (III) in a solvent under an inert atmosphere in the presence of a catalyst, an organic ligand and base, thereby obtaining the compound shown as the formula (I), wherein the structural formula is as shown in the description; R1 and R2 are respectively and independently selected from H, C1-C6 alkyl, C1-C6 alkoxy or halogens; R3 refers to C6-C10 aryl or C5-C8 heterocyclic aryl; the C6-C10 aryl or C5-C8 heterocyclic aryl is optionally substituted by 1-3 substituent groups; and the substituent groups refer to C1-C6 alkyl or halogens. The method achieves good effects due to the selection of the proper catalyst, organic ligand, base and solvent and has wide industrial application prospects.

Description

technical field [0001] The present invention relates to a method for synthesizing condensed ring compounds, more specifically to a method for synthesizing pharmaceutical intermediate phenanthrene compounds, and belongs to the fields of organic synthesis and pharmaceutical intermediate synthesis. Background technique [0002] 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. [0003] It is precisely because of such excellent performance and potential of phenanthrene compounds that the research on new synthetic methods of phenanthrene and its derivatives has always been a hot issue of great concern to organic chemical synthe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B37/10C07C25/22C07C17/275C07C15/30C07C2/42C07D213/127C07D213/16
CPCC07B37/10C07C2/42C07C15/30C07C17/275C07C25/22C07D213/127C07D213/16
Inventor 翟学研
Owner NANTONG YOUYUAN ART PATTERN DESIGN CO LTD
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