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A novel synthetic method of pyrrole derivatives

A synthetic method, pyrrole technology, applied in the direction of organic chemistry, etc.

Inactive Publication Date: 2017-03-01
SHANDONG RES INST OF TUMOUR PREVENTION TREATMENT
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] As mentioned above, a variety of methods for synthesizing pyrrole derivatives have been disclosed in the prior art, but there is still a need for continued research on new synthetic methods for pyrrole derivatives

Method used

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  • A novel synthetic method of pyrrole derivatives
  • A novel synthetic method of pyrrole derivatives
  • A novel synthetic method of pyrrole derivatives

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035]

[0036] At room temperature, add 100mmol of the above formula (I) compound, 100mmol of the above formula (II) compound, 100mmol of the above formula (III) compound, 4mmol of the catalyst Pd(MeCN) in the appropriate amount of organic solvent acetonitrile in the reactor 2 Cl 2 , 200mmol base N-(4-pyridylmethyl)ethylamine and 10mmol accelerator (a mixture of 2.5mmol copper trifluoromethanesulfonate and 7.5mmol yttrium nitrate), then warming up to 60°C, and stirring the reaction at this temperature 8 hours;

[0037]After the reaction, the reaction mixture was poured into deionized water, fully shaken, then extracted 2-3 times with ethyl acetate, the organic phases were combined, and the organic phases were washed with saturated brine and deionized water, and then washed with anhydrous Magnesium sulfate was dried, concentrated under reduced pressure, and the residue was separated by 200-300 mesh silica gel column chromatography, and the mixed solution of acetone and pet...

Embodiment 2

[0041]

[0042] At room temperature, add 100mmol of the above formula (I) compound, 120mmol of the above formula (II) compound, 110mmol of the above formula (III) compound, 6mmol of the catalyst Pd(MeCN) in the appropriate amount of organic solvent acetonitrile in the reactor 2 Cl 2 , 250mmol base N-(4-pyridylmethyl)ethylamine and 15mmol accelerator (a mixture of 3mmol copper trifluoromethanesulfonate and 12mmol yttrium nitrate), then warming up to 70°C, and stirring the reaction at this temperature for 6 hours ;

[0043] After the reaction, the reaction mixture was poured into deionized water, fully shaken, then extracted 2-3 times with ethyl acetate, the organic phases were combined, and the organic phases were washed with saturated brine and deionized water, and then washed with anhydrous Magnesium sulfate was dried, concentrated under reduced pressure, and the residue was separated by 200-300 mesh silica gel column chromatography, and the mixed solution of acetone and ...

Embodiment 3

[0047]

[0048] At room temperature, in the appropriate amount of organic solvent acetonitrile in the reactor, add 100mmol of the above formula (I) compound, 150mmol of the above formula (II) compound, 120mmol of the above formula (III) compound, 8mmol of the catalyst Pd (MeCN) 2 Cl 2 , 300mmol base N-(4-pyridylmethyl)ethylamine and 20mmol accelerator (a mixture of 4.5mmol copper trifluoromethanesulfonate and 15.5mmol yttrium nitrate), then warming up to 90°C, and stirring the reaction at this temperature 4 hours;

[0049] After the reaction, the reaction mixture was poured into deionized water, fully shaken, then extracted 2-3 times with ethyl acetate, the organic phases were combined, and the organic phases were washed with saturated brine and deionized water, and then washed with anhydrous Magnesium sulfate was dried, concentrated under reduced pressure, and the residue was separated by 200-300 mesh silica gel column chromatography, and the mixed solution of acetone and...

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Abstract

The invention relates to a synthetic method of pyrrole derivatives as shown in the following formula (IV) in specification. The synthetic method comprises the following steps of reacting a compound (I), a compound (II), and a compound (III) of the following formula (IV) under the condition that a catalyst, alkali, and an accelerant exist in an organic solvent, so as to obtain the compound of the formula (IV), wherein R1 is H, C1-C6 alkyl, halogen or nitryl; R2 is C1-C6 alkyl or benzyl. The method achieves the purpose of improving the reaction yield by creatively utilizing the compound option and composition of the catalyst, the alkali, the accelerant, and the organic solvent, so that a target product can be obtained with high yield, and the method has wide industrialization application prospect in the field of organic synthesis.

Description

technical field [0001] The invention relates to a synthesis method of heterocyclic compounds, more particularly to a three-component synthesis method of pyrrole derivatives, belonging to the field of organic intermediate synthesis. Background technique [0002] Among the heterocyclic compounds, pyrrole is an important class of compounds. As the core structure, it often appears in a large number of natural products, active alkaloids, drugs and agricultural preparations. In addition, pyrrole compounds are often used as biologically active compounds. Synthetic intermediates. [0003] It is based on such an important role of pyrrole compounds, therefore, the development of preparation methods of pyrrole derivatives has increasingly become a hot issue in the field of organic synthesis. [0004] At present, there are many existing reports on the synthesis of pyrrole derivatives in the prior art, such as: [0005] CN104710339A discloses a preparation method of 2,3,4-trisubstitute...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/06
CPCC07D401/06
Inventor 王秀芹王秀华
Owner SHANDONG RES INST OF TUMOUR PREVENTION TREATMENT