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A kind of pyridyl bridged pyrazolyl indole derivative and its preparation and application

A technology of pyridyl bridged pyrazolyl indole derivatives and pyrazolyl pyridine, which is applied in the field of preparation of pyridyl bridged pyrazolyl indole derivatives, and achieves easy availability of raw materials, high synthesis efficiency, and cheap raw materials Effect

Active Publication Date: 2020-07-14
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In recent years, a series of asymmetric and chiral pyridyl bridged tridentate ligands have been successfully prepared (Z.K.Yu, etal. Organometallics 2008, 27, 2898; Chem. Eur. J. 2012, 18, 10843; 35,1251.), and its ruthenium complexes can be applied to catalyze the transfer hydrogenation of ketones, the dehydrogenation of secondary alcohols, and the carbon-carbon bond construction reactions based on the hydrogen-borrowing strategy, and have achieved very good results, while the ruthenium metal complexes There are few reports on the dehydrogenation of nitrogen heterocycles catalyzed by

Method used

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  • A kind of pyridyl bridged pyrazolyl indole derivative and its preparation and application
  • A kind of pyridyl bridged pyrazolyl indole derivative and its preparation and application
  • A kind of pyridyl bridged pyrazolyl indole derivative and its preparation and application

Examples

Experimental program
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Effect test

Embodiment 1

[0023]

[0024] In a 25mL Schlenk reaction flask, 2-bromo-6-(3,5-dimethylpyrazole)pyridine 2a (252mg, 1.0mmol), indole 3a (117mg, 1.0mmol), cuprous bromide ( 14mg, 0.01mmol), 1,10-o-diphenanthroline (36mg, 0.02mmol), sodium carbonate (159mg, 1.5mmol) and 1,4-dioxane (5mL), stirred at 100°C for 10 hours. After the reaction, the mixture was cooled to room temperature, and the volatile components were removed under reduced pressure, and then separated by silica gel column chromatography (eluent was petroleum ether (60-90°C) / ethyl acetate, v / v=30:1 ) to obtain the target product 1a (228 mg, yield 79%) as a white solid. The target product was confirmed by NMR and high-resolution mass spectrometry.

Embodiment 2

[0026] The reaction steps and operations were the same as in Example 1, except that the reaction catalyst was CuOAc, the reaction was stopped, and the target product 1a (167 mg, yield 58%) was obtained by post-processing in the same way. It shows that when CuOAc is used as catalyst, the reaction yield decreases.

Embodiment 3

[0028] The reaction steps and operations were the same as in Example 1, except that the reaction solvent was o-xylene, the reaction was stopped, and the target product 1a (150 mg, yield 52%) was obtained by post-processing in the same way. It shows that the use of o-xylene as a solvent reduces the reaction yield.

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Abstract

The invention discloses a preparation method of pyridyl bridged pyrazolyl indole derivatives. Using 2-bromo-6-pyrazolylpyridine as a starting material, the target pyridyl-bridged pyrazolylindole derivatives were synthesized by a simple substitution reaction. These compounds can be used as tridentate ligands for the synthesis of highly efficient catalysts for the dehydrogenation of saturated nitrogen heterocycles. The invention has the advantages of cheap and easy-to-obtain raw materials, high synthesis efficiency, easy derivatization of products, and the like.

Description

technical field [0001] The invention relates to a preparation method of pyridyl bridged pyrazolyl indole derivatives. Electron-rich pyridyl bridged pyrazolyl indole derivatives were prepared by substitution reaction of 2-bromo-6-pyrazolylpyridine with indole compounds. The invention has the advantages of cheap and easy-to-obtain raw materials, high synthesis efficiency, easy derivatization of products, and the like. The pyridyl bridged pyrazolyl indole derivatives can be used in the preparation of ruthenium metal complex catalysts, and can be used to catalyze the dehydrogenation reaction of saturated nitrogen heterocyclic rings. [0002] technical background [0003] Nitrogen-containing heterocyclic compounds are a very important class of organic compounds, which are widely used in medicine, organic light-emitting materials, dyes and other fields. Traditional synthesis methods of nitrogen heterocyclic compounds often require equivalent oxidants and tedious experimental step...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/14B01J31/24C07D215/04
CPCB01J31/24B01J2231/76B01J2531/0244B01J2531/821C07D215/04C07D401/14
Inventor 王清福余正坤
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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