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A kind of synthetic method of formyl heteroaromatic drug intermediate compound

A technology for the synthesis of formyl heteroaromatic hydrocarbons and synthesis methods, which is applied in the synthesis of heteroaromatic compounds and the synthesis of formyl heteroaromatic drug intermediate compounds. It can solve the problems of few reports on formylation modification methods and achieve excellent technology effect of effect

Active Publication Date: 2016-08-31
长治市武理工工程技术研究院
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Although there are many synthetic processes for pyridine derivatives, there are few reports on the formylation modification of such compounds.

Method used

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  • A kind of synthetic method of formyl heteroaromatic drug intermediate compound
  • A kind of synthetic method of formyl heteroaromatic drug intermediate compound
  • A kind of synthetic method of formyl heteroaromatic drug intermediate compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033]

[0034] In a dry reaction vessel, add an appropriate amount of organic solvent toluene, then add 100mmol formula (II) compound, 2mmol copper trifluoroacetylacetonate, 100mmol formula (III) compound, 200mmol TBHP and 5mmol reaction auxiliary (4.2mmol N- A mixture of butylpyridine sulfonate p-toluenesulfonate and 0.8 mmol cyclooctene tricarbonyl iron), the temperature was raised to 70° C., and the reaction was carried out at this temperature for 12 hours.

[0035] After completion of the reaction, cool to room temperature naturally, then add saturated aqueous sodium bicarbonate solution to wash fully, separate the organic phase, dry with anhydrous magnesium sulfate, then concentrate under reduced pressure, and the residue is separated by silica gel column chromatography (wherein the column chromatography is used for washing Dehydration is a mixture of ethyl acetate and n-propanol, the volume ratio of the two is 10:1), and the compound of formula (I) is obtained with a ...

Embodiment 2

[0039]

[0040] In a dry reaction vessel, add an appropriate amount of organic solvent chlorobenzene, then add 100mmol formula (II) compound, 150mmol formula (III) compound, 4mmol copper trifluoroacetylacetonate, 220mmol TBHP and 7mmol reaction auxiliary (6.2mmol N - a mixture of butylpyridine sulfonate p-toluenesulfonate and 0.8 mmol of cyclooctatetraenetricarbonyliron), raise the temperature to 80° C., and react at this temperature for 10 hours.

[0041] After completion of the reaction, cool to room temperature naturally, then add saturated aqueous sodium bicarbonate solution to wash fully, separate the organic phase, dry with anhydrous magnesium sulfate, then concentrate under reduced pressure, and the residue is separated by silica gel column chromatography (wherein the column chromatography is used for washing Dehydration is a mixture of ethyl acetate and n-propanol, the volume ratio of which is 10:2), and the compound of formula (I) is obtained with a yield of 98.6%. ...

Embodiment 3

[0045]

[0046] In a dry reaction vessel, add an appropriate amount of organic solvent N-methylpyrrolidone, then add 100mmol formula (II) compound, 200mmol formula (III) compound, 6mmol copper trifluoroacetylacetonate, 240mmol TBHP and 8mmol reaction auxiliary agent (for 7.25 mmol of N-sulfonic acid butylpyridine p-toluenesulfonate and 0.75 mmol of cyclooctatetraene tricarbonyl iron), the temperature was raised to 100° C., and the reaction was carried out at this temperature for 8 hours.

[0047] After completion of the reaction, cool to room temperature naturally, then add saturated aqueous sodium bicarbonate solution to wash fully, separate the organic phase, dry with anhydrous magnesium sulfate, then concentrate under reduced pressure, and the residue is separated by silica gel column chromatography (wherein the column chromatography is used for washing Dehydration is a mixture of ethyl acetate and n-propanol, the volume ratio of the two is 10:1), and the compound of form...

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Abstract

The invention relates to a method for synthesizing a formyl heterocyclic aromatic drug intermediate compound shown as a formula (I) in the specification. The method comprises the following step: enabling a compound of a formula (II) in the specification to react with a compound of a formula (III) in the specification in an organic solvent in the presence of a catalyst, an oxidant and reaction aids, thereby obtaining the compound of the formula (I), wherein R1, R2, R3 and R4 are respectively and independently selected from H, C1-C6 alkyl, C1-C6 alkoxy, phenyl or nitro. According to the method, the catalyst, oxidant, reaction aids and reaction substrate are selected and combined, so that formylation at a specific site is realized, and the method has high yield and has wide application prospects and potentials in the field of synthetic methods of drug intermediates.

Description

technical field [0001] The present invention relates to a method for synthesizing heteroaromatic compounds containing acyl groups, more specifically to a method for synthesizing formyl heteroaromatic drug intermediate compounds, and belongs to the fields of organic synthesis and pharmaceutical intermediate synthesis. Background technique [0002] In the field of organic chemical synthesis, especially in the field of medicinal chemistry, the structure of methyl heteroaryls can be applied to the synthesis and design of various heteroaryl derivatives. For example, the imidazopyridine structure is a ubiquitous natural product or structural units in synthetic drugs, which exist in the drug structures of zolpidem, alpitant, oprenone, etc. and have shown a wide range of biological activities. It can be seen that the development of such formylated products It will have a positive and far-reaching impact on the field of drug synthesis. [0003] So far, a large number of scientific r...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 陈政华
Owner 长治市武理工工程技术研究院
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