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Pyridyl bridging pyrazolyl pyrrole derivative, preparation and application

A technology of pyridyl-bridged pyrazolylpyridine and pyrazolylpyridine is applied in the field of preparation of pyridyl-bridged pyrazolylpyrrole derivatives, which can solve the problems of cumbersome experimental steps, equivalent weight and the like, and achieves easy availability of raw materials, Inexpensive effect

Active Publication Date: 2018-10-02
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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Problems solved by technology

Traditional alcohol oxidation methods often require equivalent oxidants and tedious experimental steps

Method used

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  • Pyridyl bridging pyrazolyl pyrrole derivative, preparation and application
  • Pyridyl bridging pyrazolyl pyrrole derivative, preparation and application
  • Pyridyl bridging pyrazolyl pyrrole derivative, preparation and application

Examples

Experimental program
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Effect test

Embodiment 1

[0023]

[0024] In a 25mL Schlenk reaction flask, add 2-bromo-6-(3,5-dimethylpyrazole)pyridine 2a (252mg, 1.0mmol), pyrrole 3a (134mg, 2.0mmol), cuprous iodide (38mg , 0.02mmol), 1,10-o-diphenanthroline (72mg, 0.04mmol), sodium carbonate (212mg, 2.0mmol) and toluene (5mL), stirred at 90°C for 12 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=20:1 ), to obtain the target product 1a (190 mg, yield 80%) 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 CuCl, the reaction was stopped, and the target product 1a (162 mg, yield 68%) was obtained by post-processing in the same way. It shows that when CuCl 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 acetonitrile, the reaction was stopped, and the target product 1a (110 mg, yield 46%) was obtained by post-processing in the same way. It shows that using acetonitrile as solvent, the reaction yield will decrease.

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Abstract

The invention discloses a preparation method of a pyridyl bridging pyrazolyl pyrrole derivative. According to the preparing method, 2-bromine-6-pyrazolyl pyrrole is used as a raw material, and the target pyridyl bridging pyrazolyl pyrrole derivative is synthesized through a simple substitution reaction. The pyridyl bridging pyrazolyl pyrrole derivative can be used as tridentate ligand for synthesizing an efficient alcohol dehydrogenase catalyst. The preparing method of the pyridyl bridging pyrazolyl pyrrole derivative has the advantages that the raw material is cheap and easy to obtain, the synthesizing efficiency is high, and derivation of the product is easy.

Description

technical field [0001] The invention relates to a preparation method of pyridyl bridged pyrazolylpyrrole derivatives. Using 2-bromo-6-pyrazolylpyridine as raw material to undergo substitution reaction with pyrrole compound to prepare electron-rich pyridyl bridged pyrazolylpyrrole derivatives. 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 pyrazolylpyrrole derivative can be used in the preparation of ruthenium metal complex catalysts, and can be used to catalyze alcohol dehydrogenation reactions. technical background [0002] The oxidative dehydrogenation of alcohols is a very important chemical reaction. Traditional alcohol oxidation methods often require equivalent oxidants and tedious experimental steps. Alcohol dehydrogenation reactions catalyzed by metal complexes in the absence of oxidants have attracted extensive attention in recent years. The ...

Claims

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Application Information

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IPC IPC(8): C07D401/14B01J31/24C07C45/00C07C49/78
CPCB01J31/24B01J2231/76B01J2531/0244B01J2531/821C07C45/002C07D401/14C07C49/78
Inventor 王清福余正坤
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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