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A kind of catalytic synthesis method of indane-1,3-diketone compound

A synthesis method and indane technology are applied in the preparation of organic compounds, organic compounds/hydrides/coordination complex catalysts, preparation of carbon-based compounds, etc., and can solve the synthetic requirements and reaction conditions of organic synthetic pharmaceutical compounds that cannot be met. Harshness, long reaction time and other problems, to achieve the effect of satisfying industrial production, improving yield and realizing high-speed conversion

Active Publication Date: 2017-03-22
南陵县生产力促进中心有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] However, these existing technologies often have disadvantages such as harsh reaction conditions, low yields, and long reaction times, which cannot meet the needs of organic synthesis, especially the synthesis of a large number of pharmaceutical compounds.

Method used

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  • A kind of catalytic synthesis method of indane-1,3-diketone compound
  • A kind of catalytic synthesis method of indane-1,3-diketone compound
  • A kind of catalytic synthesis method of indane-1,3-diketone compound

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Experimental program
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Effect test

Embodiment 1

[0031]

[0032] At room temperature, to an appropriate amount of organic solvent DMAc (N,N-dimethylacetamide), add 100 mmol of the above formula (I) compound, 8 mmol of catalyst PdCl 2 (Py) 2 , 150mmol oxidant silver trifluoroacetate, 10mmol organic ligand L1 and 15mmol auxiliary agent triethanolamine borate, and then replace it with nitrogen several times until the reaction atmosphere is nitrogen atmosphere; raise the temperature to 80°C, and fully Stirring and reacting for 9 hours;

[0033] After the reaction, the reaction liquid was naturally cooled to room temperature, filtered, and the pH value of the filtrate was adjusted to neutral, washed with saturated brine, then extracted with ethyl acetate for 2-3 times, combined with organic phases, dried over anhydrous sodium sulfate, Concentration under reduced pressure, the resulting residue was subjected to 300-400 mesh silica gel column chromatography, and eluted with a mixture of dichloromethane and acetone at a volume r...

Embodiment 2

[0036] Reaction formula is with embodiment 1, and concrete reaction process is as follows:

[0037] At room temperature, add 100 mmol of the above formula (I) compound, 10 mmol of the catalyst PdCl to an appropriate amount of organic solvent DMAc (N,N-dimethylacetamide) 2 (Py) 2 , 200mmol oxidant silver trifluoroacetate, 14mmol organic ligand L1 and 20mmol auxiliary agent triethanolamine borate, and then replace it with nitrogen several times until the reaction atmosphere is nitrogen atmosphere; raise the temperature to 85°C, and fully Stirring and reacting for 8 hours;

[0038]After the reaction, the reaction liquid was naturally cooled to room temperature, filtered, and the pH value of the filtrate was adjusted to neutral, washed with saturated brine, then extracted with ethyl acetate for 2-3 times, combined with organic phases, dried over anhydrous sodium sulfate, Concentration under reduced pressure, the resulting residue was subjected to 300-400 mesh silica gel column c...

Embodiment 3

[0041] Reaction formula is with embodiment 1, and concrete reaction process is as follows:

[0042] At room temperature, add 100 mmol of the above formula (I) compound, 12 mmol of catalyst PdCl to an appropriate amount of organic solvent DMAc (N,N-dimethylacetamide) 2 (Py) 2 , 250mmol oxidant silver trifluoroacetate, 18mmol organic ligand L1 and 25mmol auxiliary agent triethanolamine borate, and then replace it with nitrogen several times until the reaction atmosphere is nitrogen atmosphere; raise the temperature to 90°C, and fully Stirring and reacting for 6 hours;

[0043] After the reaction, the reaction liquid was naturally cooled to room temperature, filtered, and the pH value of the filtrate was adjusted to neutral, washed with saturated brine, then extracted with ethyl acetate for 2-3 times, combined with organic phases, dried over anhydrous sodium sulfate, Concentration under reduced pressure, the resulting residue was subjected to 300-400 mesh silica gel column chro...

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Abstract

The present invention relates to a formula (II) shown hydrindene-1,3-dione compound catalysis synthetic method which is as follows: in an organic solvent and under a nitrogen atmosphere, in the presence of a catalyst, an oxidant, and an organic ligand and an adjuvant, self cyclization of a formula (I) compound is performed, the formula (II) compound is obtained by after-treatment after the end of the reaction, the method uses the new catalyst, the oxidant, the organic ligand, the organic solvent and the adjuvant for comprehensive selection and optimization to achieve material high-speed conversion, the yield of the target product can be greatly improved, the needs of industrial production can be better met, and the method has a broad market prospect.

Description

technical field [0001] The invention relates to a catalytic synthesis method of indane-1,3-dione compound, which belongs to the field of organic chemical synthesis. Background technique [0002] In the field of organic chemical synthesis, indane-1,3-dione compound occupies a very important position, and various downstream products and pharmaceutical intermediates can be prepared through this compound, for example, indane-1,3-dione The derivatives of ketones have various biological activities, such as: P1 kinase inhibitory effect, anti-allergy, CDK inhibitor, etc., so they can be used in the preparation of various drugs. [0003] With the continuous development and progress in the field of medicine, the importance of indane-1,3-dione derivatives is self-evident, and a large number of researchers have carried out in-depth exploration of their preparation methods. There are already some classic synthesis processes of indane-1,3-dione compounds in the prior art, such as: [00...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/00C07C45/61C07C49/67B01J31/24
CPCB01J31/24B01J2231/30C07C45/00C07C45/455C07C45/516C07C45/61C07C49/67
Inventor 刘军王刚毛慧
Owner 南陵县生产力促进中心有限公司
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