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A kind of synthetic method of pharmaceutical intermediate condensed heterocyclic ketone compound

A synthetic method and compound technology, which is applied in the synthesis of ketone compounds, organic synthesis, and the synthesis of fused heterocyclic ketone compounds as pharmaceutical intermediates, achieving the effects of broad market prospects, short process time and high yield

Active Publication Date: 2017-09-22
CHENGDU ORGANOCHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] As mentioned above, there are already some synthetic methods of heterocyclic ketones in the prior art, but for the new synthetic methods of this type of compounds, there is still a need for further research

Method used

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  • A kind of synthetic method of pharmaceutical intermediate condensed heterocyclic ketone compound
  • A kind of synthetic method of pharmaceutical intermediate condensed heterocyclic ketone compound
  • A kind of synthetic method of pharmaceutical intermediate condensed heterocyclic ketone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033]

[0034] At room temperature, add 100mmol of the above formula (I) compound, 150mmol of the above formula (II) compound, 6mmol of the catalyst (4mmol Ru 3 (CO) 12 with 2mmol of porphyrin), 30mmol of auxiliary agent (as a mixture of 25mmol of 2-fluorophenylboronic acid pinacol ester and 5mmol of 1,2-bis(triethoxysilyl)ethane) and 100mmol of base DMEDA, and then Heat up to 70°C and fully stir the reaction at this temperature for 10 hours;

[0035] After the reaction is completed, cool the reaction system to room temperature naturally, then adjust the pH value of the system to 6.5-7, then fully shake and wash with deionized water, then add chloroform to extract 2-3 times, combine the organic phases, and dry with anhydrous magnesium sulfate , Distilled under reduced pressure, the residue was chromatographed on a 300-400 mesh silica gel column, with a mixture of ethyl acetate and acetone at a volume ratio of 1:2 as the eluent, TLC detected the elution end point, collect...

Embodiment 2

[0038]

[0039] At room temperature, add 100mmol of the above formula (I) compound, 175mmol of the above formula (II) compound, 7.5mmol of the catalyst (for 5 mmol Ru 3 (CO) 12 with 2.5mmol of porphyrin), 39mmol of auxiliary agent (as a mixture of 26mmol of 2-fluorophenylboronic acid pinacol ester and 13mmol of 1,2-bis(triethoxysilyl)ethane) and 150mmol of base DMEDA, and then Heat up to 75°C and fully stir the reaction at this temperature for 8 hours;

[0040] After the reaction is completed, cool the reaction system to room temperature naturally, then adjust the pH value of the system to 6.5-7, then fully shake and wash with deionized water, then add chloroform to extract 2-3 times, combine the organic phases, and dry with anhydrous magnesium sulfate , Distilled under reduced pressure, the residue was chromatographed on a 300-400 mesh silica gel column, with a mixture of ethyl acetate and acetone at a volume ratio of 1:2 as the eluent, TLC detected the elution end point...

Embodiment 3

[0043]

[0044] At room temperature, add 100mmol of the above formula (I) compound, 200mmol of the above formula (II) compound, 9.9mmol of catalyst (for 6.6 mmol Ru 3 (CO) 12 with 3.3mmol of porphyrin), 50mmol of auxiliary agent (as a mixture of 37.5mmol of 2-fluorophenylboronic acid pinacol ester and 12.5mmol of 1,2-bis(triethoxysilyl)ethane) and 200mmol of base DMEDA , then warming up to 80°C and fully stirring the reaction at this temperature for 6 hours;

[0045] After the reaction is completed, cool the reaction system to room temperature naturally, then adjust the pH value of the system to 6.5-7, then fully shake and wash with deionized water, then add chloroform to extract 2-3 times, combine the organic phases, and dry with anhydrous magnesium sulfate , Distilled under reduced pressure, the residue was chromatographed on a 300-400 mesh silica gel column, with a mixture of ethyl acetate and acetone at a volume ratio of 1:2 as the eluent, TLC detected the elution end...

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Abstract

The invention relates to a synthesis method for a condensed heterocyclic compound as shown in a formula (III) in the specification. The method comprises the following steps: adding a compound as shown in a formula (I), a compound as shown in a formula (II), a catalyst, auxiliaries and alkaline to an organic solvent under a room temperature, and then heating to 70 to 80 DEG C and sufficiently stirring to react for 6 to10 hours to obtain the compound as shown in the formula (III), wherein R1 is C1-C6 alkyls or unsubstituted or substituent-containing phenyl; R2 is C1-C6 alkoxy, C6-C12 alkyl or phenyl. According to the method disclosed by the invention, an unexpected effect of high yield can be produced by means of compressive selection and coordination of the catalyst, the auxiliaries, the alkaline and the organic solvent, and the process time is relatively short and is favorable to meet the demand on low energy consumption in the industrial production; the method disclosed by the invention has a wide market prospect and has an industrial application potential in the field of organic chemical synthesis, in particular to the field of synthesis of medicine intermediates.

Description

technical field [0001] The invention relates to a method for synthesizing ketone compounds, more particularly to a method for synthesizing pharmaceutical intermediates of condensed heterocyclic ketones, belonging to the field of organic synthesis, especially the synthesis of pharmaceutical intermediates. Background technique [0002] In the technical field of organic chemical synthesis, especially the synthesis of pharmaceutical intermediates, heterocyclic ketones have an important role and status, and they can usually be used as synthetic intermediates of final drugs. [0003] It is precisely because of such an important role of this type of compound that people have conducted a lot of research on its synthesis and achieved some results, such as: [0004] Franca M. Cordero et al. (“New Synthesis of by Ethylene Extrusionfrom Spirocyclopropane Isoxazolidines", J.Am.Chem.Soc., 2000,122,8075-8076) reported a method for preparing β-aminoketones by splitting the N-O bond, and i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/36
CPCC07D209/36
Inventor 谈平忠谈平安周永恒马飞陈军
Owner CHENGDU ORGANOCHEM CO LTD
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