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Synthetic method of medical intermediate diaryl ketone compound

A synthesis method and a technology for diaryl ketones are applied in the synthesis of ketone compounds and in the field of synthesis of diaryl ketone compounds, which can solve the problems such as the yield needs to be improved, the substrate needs to be expanded, etc., to achieve the expansion of material sources and high efficiency Preparation, the effect of broad industrial prospects

Inactive Publication Date: 2017-01-04
黄程
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] As mentioned above, multiple methods for the synthesis of aryl ketones have been disclosed in the prior art, but these existing methods still have defects such as substrates to be expanded and yields to be improved.

Method used

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  • Synthetic method of medical intermediate diaryl ketone compound
  • Synthetic method of medical intermediate diaryl ketone compound
  • Synthetic method of medical intermediate diaryl ketone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042]

[0043] At room temperature, add 100 mmol of the above formula (I) to an appropriate amount of organic solvent (a mixture of N,N-dimethylformamide (DMF) and polyethylene glycol 200 (PEG-200) at a volume ratio of 4:1) Compound, 40mmol formula (II) compound, 11mmol catalyst bis(triphenylphosphine)cyclopentadienyl ruthenium chloride, 100mmol oxidant bis(trifluoroacetic acid) iodobenzene (PhI(TFA) 2), 20mmol organic ligand L1 and 60mmol base, 5,7-triazabicyclo[4.4.0]dec-5-ene (TBD), then heated to 70°C under stirring, and stirred at this temperature for reaction 12 Hour;

[0044] After the reaction was completed, the reaction system was naturally cooled to room temperature, and the pH value was adjusted to be neutral, filtered, the filtrate was washed with saturated brine, and then extracted with ethyl acetate for 2-3 times, the organic phases were combined, dried over anhydrous sodium sulfate, Concentrated under reduced pressure, the residue was subjected to silica ge...

Embodiment 2

[0047]

[0048] At room temperature, add 100 mmol of the above formula (I) to an appropriate amount of organic solvent (a mixture of N,N-dimethylformamide (DMF) and polyethylene glycol 200 (PEG-200) at a volume ratio of 4:1) Compound, 80mmol formula (II) compound, 7mmol catalyst bis(triphenylphosphine) cyclopentadienyl ruthenium chloride, 150mmol oxidant bis(trifluoroacetic acid) iodobenzene (PhI(TFA) 2 ), 10mmol organic ligand L1 and 100mmol base, 5,7-triazabicyclo[4.4.0]dec-5-ene (TBD), then heated to 100°C under stirring, and stirred at this temperature for 8 Hour;

[0049] After the reaction was completed, the reaction system was naturally cooled to room temperature, and the pH value was adjusted to be neutral, filtered, the filtrate was washed with saturated brine, and then extracted with ethyl acetate for 2-3 times, the organic phases were combined, dried over anhydrous sodium sulfate, Concentrate under reduced pressure, and the residue is subjected to silica gel col...

Embodiment 3

[0052]

[0053] At room temperature, add 100 mmol of the above formula (I) to an appropriate amount of organic solvent (a mixture of N,N-dimethylformamide (DMF) and polyethylene glycol 200 (PEG-200) at a volume ratio of 4:1) Compound, 60mmol formula (II) compound, 8mmol catalyst bis(triphenylphosphine) cyclopentadienyl ruthenium chloride, 120mmol oxidant bis(trifluoroacetic acid) iodobenzene (PhI(TFA) 2 ), 15mmol organic ligand L1 and 80mmol base, 5,7-triazabicyclo[4.4.0]dec-5-ene (TBD), then heated to 80°C under stirring, and stirred at this temperature for reaction 11 Hour;

[0054] After the reaction was completed, the reaction system was naturally cooled to room temperature, and the pH value was adjusted to be neutral, filtered, the filtrate was washed with saturated brine, and then extracted with ethyl acetate for 2-3 times, the organic phases were combined, dried over anhydrous sodium sulfate, Concentrate under reduced pressure, and the residue is subjected to silica...

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Abstract

The invention relates to a synthetic method of a diaryl ketone compound which can be used as a medical intermediate and is as shown in the formula (III). The method comprises the following steps: in an organic solvent and in the presence of a catalyst, an oxidizing agent, an organic ligand and alkali, a compound as shown in the formula (I) and a compound as shown in the formula (II) react; and after the reaction, the reaction product undergoes postprocessing so as to obtain the compound as shown in the formula (III). In the formula (III), R1 is selected from H, C1-C6 alkyl group or C1-C6 alkoxy group; R2 is selected from C1-C6 alkyl group or unsubstituted or phenyl group bearing substituent group, wherein the substituent group is C1-C6 alkyl group or halogen; and X is halogen. According to the method, novel reaction materials and catalytic system are adopted. Through integrated collaboration of multiple characteristics, efficient preparation of the diaryl ketone compound is realized. Sources of materials are widened, and yield of the product is raised. The synthetic method has a wide industrial prospect.

Description

technical field [0001] The invention relates to a method for synthesizing ketone compounds, more particularly to a method for synthesizing diaryl ketone compounds that can be used as pharmaceutical intermediates, and belongs to the technical field of organic chemistry, especially the synthesis of pharmaceutical intermediates. Background technique [0002] Aryl ketones are usually used to construct the structures of natural products and bioactive molecules with pharmaceutical activity (such as drugs with anti-inflammatory activity in the figure below), so they have attracted much attention in the field of drug synthesis and design. [0003] [0004] Just because the molecular structure of drugs needs to contain such structural units, aryl ketones have good application prospects and practical value in the field of drug synthesis. [0005] Therefore, the development of new and efficient synthetic methods for aryl ketones will have a positive impact on the development and pro...

Claims

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Application Information

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IPC IPC(8): C07C45/45C07C49/784C07C49/813C07C49/213
CPCC07C45/45C07C49/784C07C49/813C07C49/213
Inventor 不公告发明人
Owner 黄程
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