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Polysubstituted benzothienopyridine compound and preparation method thereof

A technology of phenopyridine and benzothiopyridine, which is applied in the field of multi-substituted thienopyridine compounds and their preparation, can solve the problems of reaction research limitations and achieve the effects of high atom economy, high step economy and convenient operation

Inactive Publication Date: 2021-04-02
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In comparison, studies involving reactions between carbon prenucleophiles and nitriles are more limited, and most reactions require the participation of high temperature or transition metal catalysts

Method used

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  • Polysubstituted benzothienopyridine compound and preparation method thereof
  • Polysubstituted benzothienopyridine compound and preparation method thereof
  • Polysubstituted benzothienopyridine compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Add 0.2 mmol 2-methyl-3-(phenylethynyl) benzo[b]thiophene, 0.6 mmol benzonitrile, 0.4 mmol bis(trimethylsilyl) lithium amide, 0.24 Millimoles of potassium tert-butoxide and 0.5 ml of anhydrous cyclopentyl methyl ether solvent were stirred and reacted at 120 degrees Celsius at 500 rpm for 24 hours, and the stirring was stopped. Add 5 mL of water, extract 3 times with ethyl acetate, combine the organic phases and use 0.5 g of anhydrous sodium sulfate to dry, filter, concentrate under reduced pressure, and then separate and purify by column chromatography to obtain the target product, which is eluted by column chromatography The liquid is petroleum ether:ethyl acetate mixed solvent with a volume ratio of 100:1, and the yield is 90%.

[0045] The hydrogen spectrogram and the carbon spectrogram of the product obtained in this embodiment are respectively as follows figure 1 and figure 2 shown; the structural characterization data are shown below:

[0046] 1 H NMR (400MHz...

Embodiment 2

[0053] Add 0.2 mmol 3-((4-methoxyphenyl)ethynyl)-2-methylbenzo[b]thiophene, 0.6 mmol benzonitrile, 0.4 mmol bis(trimethyl Silicon-based) lithium amide, 0.24 mmol of potassium tert-butoxide and 0.5 ml of anhydrous cyclopentyl methyl ether solvent were stirred and reacted at 120 degrees Celsius at 500 rpm for 24 hours, and the stirring was stopped. Add 5 mL of water, extract 3 times with ethyl acetate, combine the organic phases and use 0.5 g of anhydrous sodium sulfate to dry, filter, concentrate under reduced pressure, and then separate and purify by column chromatography to obtain the target product, which is eluted by column chromatography The liquid is petroleum ether with a volume ratio of 40:1: ethyl acetate mixed solvent, and the yield is 71%.

[0054] The hydrogen spectrogram and the carbon spectrogram of the product obtained in this embodiment are respectively as follows image 3 and Figure 4 shown; the structural characterization data are shown below:

[0055] 1 ...

Embodiment 3

[0062] Add 0.2 mmol N,N-dimethyl-4-((2-methylbenzo[b]thiophen-3-yl)ethynyl)aniline to the reaction tube, 0.6 mmol benzonitrile, 0.4 mmol Lithium bis(trimethylsilyl)amide, 0.24 mmol potassium tert-butoxide and 0.5 ml anhydrous cyclopentyl methyl ether solvent were stirred and reacted at 120 degrees Celsius at 500 rpm for 24 hours, and the stirring was stopped. Add 5 mL of water, extract 3 times with ethyl acetate, combine the organic phases and use 0.5 g of anhydrous sodium sulfate to dry, filter, concentrate under reduced pressure, and then separate and purify by column chromatography to obtain the target product, which is eluted by column chromatography The liquid is sherwood oil with a volume ratio of 10:1: ethyl acetate mixed solvent, and the yield is 83%.

[0063] The hydrogen spectrogram and the carbon spectrogram of the product obtained in this embodiment are respectively as follows Figure 5 and Figure 6 shown; the structural characterization data are shown below:

...

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Abstract

The invention belongs to the technical field of organic synthesis, and discloses a polysubstituted benzothienopyridine compound and a preparation method thereof. The preparation method comprises the steps of dissolving nitrile amino metal salt and alkali in an organic solvent in a reactor, stirring to react at the temperature of 90-130 DEG C, and separating and purifying the reaction product to obtain the polysubstituted benzothienopyridine compound, wherein the reaction formula of the preparation method is shown as a formula (I) in the description. According to the method disclosed by the invention, a series of polysubstituted benzothienopyridine compounds are synthesized by taking simple and readily available 2-methyl-3-alkynyl benzothiophene and nitrile as reaction raw materials. The method has the characteristics of simple and readily available raw materials, convenience in operation, no transition metal, high step economy, high atom economy, wide substrate applicability, good tolerance of functional groups and the like; and part of application research is carried out, and a derivative product of a drug molecule citalopram is synthesized.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a multi-substituted thienopyridine compound and a preparation method thereof. Background technique [0002] Benzothienopyridine compounds have rich potential drugs and biological activities because they contain two heterocyclic skeletons of thiophene and pyridine. At the same time, the existence of the pyridine ring can also make it participate in the design and synthesis of new catalysts in the form of monodentate nitrogen ligands. In addition, a class of bidentate or tridentate can be selectively synthesized according to the modification of the 1,3-position substituent. nitrogen ligand. Through literature research, the current methods for synthesizing benzothienopyridines are relatively limited, mainly including: (1) regioselective cyclization reaction of internal alkyne and aryl imine or aryl vinyl azide; (2) palladium Catalyzed sequential cyclization o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04
CPCC07D495/04
Inventor 江焕峰何丹丹伍婉卿
Owner SOUTH CHINA UNIV OF TECH
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