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Synthetic method for drug intermediate diaryl ketone compound

A synthesis method and technology of diaryl ketones, applied in the direction of organic chemistry, etc., can solve the problems of low yield and achieve high yield and broad market application prospects

Active Publication Date: 2016-04-13
江西远邦药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] As mentioned above, there have been multiple methods for the synthesis of aryl ketones in the prior art, but there are still some defects in these methods, such as too low yield etc.

Method used

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  • Synthetic method for drug intermediate diaryl ketone compound
  • Synthetic method for drug intermediate diaryl ketone compound
  • Synthetic method for drug intermediate diaryl ketone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035]

[0036] At room temperature, in a nitrogen atmosphere, add 100 mmol of the above formula (I) compound, 120 mmol of the above formula (II) compound, and 10 mmol of the catalyst NiCl to an appropriate amount of organic solvent ethylene glycol 2 (PCy 3 ) 2 , 150mmol oxidant cerium ammonium nitrate, 150mmol alkali DMPA and 10mmol accelerator (being the mixture of 2.5mmol cadmium acetate and 7.5mmol strontium nitrate), then warming up to 60°C, and stirring and reacting at this temperature for 10 hours;

[0037] After the reaction is over, filter the reaction liquid while it is hot, adjust the pH value of the filtrate to neutral, then fully wash with saturated brine, then add ethyl acetate to extract 2-3 times, combine the organic phases, dry over anhydrous sodium sulfate, reduce Concentrate under reduced pressure, and the resulting residue is subjected to silica gel column chromatography, eluting with a mixture of acetone and petroleum ether in an equal volume ratio, so...

Embodiment 2

[0040]

[0041] At room temperature, in a nitrogen atmosphere, to an appropriate amount of organic solvent ethylene glycol, add 100 mmol of the compound of the above formula (I), 150 mmol of the compound of the above formula (II), and 12 mmol of the catalyst NiCl 2 (PCy 3 ) 2 , 200mmol oxidant ceric ammonium nitrate, 175mmol alkali DMPA and 15mmol accelerator (being the mixture of 3mmol cadmium acetate and 12mmol strontium nitrate), then be warming up to 70 ℃, and at this temperature stirring reaction 8 hours;

[0042] After the reaction, the reaction solution was filtered while hot, the pH value of the filtrate was adjusted to neutral, then fully washed with saturated brine, and then extracted with ethyl acetate for 2-3 times, the organic phases were combined, dried over anhydrous sodium sulfate, reduced Concentrated under pressure, the obtained residue was subjected to silica gel column chromatography and rinsed with a mixture of acetone and petroleum ether in an equal vol...

Embodiment 3

[0045]

[0046] In a nitrogen atmosphere at room temperature, 100 mmol of the compound of the above formula (I), 180 mmol of the compound of the above formula (II), and 14 mmol of the catalyst NiCl were added to an appropriate amount of organic solvent ethylene glycol. 2 (PCy 3 ) 2 , 250mmol oxidant cerium ammonium nitrate, 200mmol alkali DMPA and 20mmol accelerator (being the mixture of 4.5mmol cadmium acetate and 15.5mmol strontium nitrate), then be warming up to 80 ℃, and at this temperature stirring reaction 6 hours;

[0047] After the reaction, the reaction solution was filtered while hot, the pH value of the filtrate was adjusted to neutral, then fully washed with saturated brine, and then extracted with ethyl acetate for 2-3 times, the organic phases were combined, dried over anhydrous sodium sulfate, reduced Concentrated under pressure, and the obtained residue was subjected to silica gel column chromatography and rinsed with a mixture of acetone and petroleum ethe...

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Abstract

The invention relates to a synthetic method for a diaryl ketone compound which can be used as a drug intermediate and is shown as a formula (III) which is described in the specification. The method comprises a step of reacting a compound (I) as described in the specification with a compound (II) as described in the specification in a nitrogen atmosphere and organic solvent in the presence of a catalyst, an oxidizing agent, alkali and a promoter so as to obtain the compound as shown in the formula (III). In the formula (III), R1, R2 and R3 are independently selected from a group consisting of H, C1-6 alkyl groups, C1-6 alkyloxy groups, halogen and nitro groups; and X is halogen. According to the method, through selection of an appropriate substrate and usage of a reaction system composed of the catalyst, the oxidizing agent, the alkali and the promoter, high yield of the target product, i.e., the diaryl ketone compound, is realized; and a brand novel synthetic method is provided for the compound, and the synthetic method has wide market application prospects.

Description

technical field [0001] The invention relates to a synthesis method of a ketone compound, more particularly to a synthesis method of a diaryl ketone compound, and belongs to the field of organic synthesis, especially the synthesis of pharmaceutical intermediates. Background technique [0002] In the field of organic synthesis, especially in the field of drug synthesis, the ketone structure is a necessary structure in many drugs and functional materials, and the structural modification or transformation method of ketone compounds is also a hot issue that scientists generally pay attention to. [0003] Among ketone compounds, aryl ketone has a very important position and function because of its dual reactivity of carbonyl and aryl, and it is often used as a drug intermediate. It is precisely because of such an important role of aryl ketones that people have conducted a lot of in-depth research on their synthesis methods, such as: [0004] ("Metal-Free Cross-Dehydrogenative Cou...

Claims

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Application Information

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IPC IPC(8): C07D217/16
CPCC07D217/16
Inventor 张伟
Owner 江西远邦药业有限公司
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