A method for preparing 2,2'-bipyridine-4,4'-(5-hexyl-2-thiophene)

A technology for bipyridine and thiophene, which is applied in the field of preparing 2,2'-bipyridine-4,4'-(5-hexyl-2-thiophene, can solve the problem of difficult separation and purification of products, unfavorable industrial production and high toxicity of intermediates and other problems, to achieve the effect of small reaction pollution, simple and effective product separation method, and low toxicity

Active Publication Date: 2016-04-27
上海惠仁(夏邑)制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the existing synthetic methods have problems such as low yield, expensive catalysts, high toxicity of intermediates, and difficult separation and purification of products, which are not conducive to industrial production

Method used

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  • A method for preparing 2,2'-bipyridine-4,4'-(5-hexyl-2-thiophene)
  • A method for preparing 2,2'-bipyridine-4,4'-(5-hexyl-2-thiophene)

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Embodiment 1

[0023] ① Preparation of zinc reagent: Add zinc chloride (ZnCl 2 ) 100g, tetrahydrofuran (THF) 400g, 200g Grignard reagent was added dropwise under stirring, and reacted at 65°C for 1h to prepare 229g of zinc reagent for use.

[0024] ②Synthesis of 2,2'-bipyridine-4,4'-(5-hexyl-2-thiophene): 57g of 4,4'-dibromo-2,2'-bipyridine, 1,2 - Bis(diphenylphosphine) ethane nickel chloride 1.1g, triphenylphosphine (P(Ph) 3 ) 170g, dimethylformamide (DMF) 570g, slowly add 229g of zinc reagent dropwise under nitrogen protection environment, react at 80°C for 1 hour, the reaction is completed, the product is cooled and filtered, the filter cake is added with 580g of petroleum ether, stirred, filtered and dried , then add 585g of dichloromethane to dissolve, add 5.85g of activated carbon for decolorization and filtration, wash the filter cake with 117g of dichloromethane, evaporate the filtrate to dryness and recrystallize (ethyl acetate:petroleum ether=1:4) to obtain 2,2'-dichloromethane P...

Embodiment 2

[0026] ① Preparation of zinc reagent: Add zinc chloride (ZnCl 2 ) 200g, tetrahydrofuran (THF) 800g, 400g of Grignard reagent was added dropwise under stirring, and reacted at 60°C for 1.5h to prepare 450g of zinc reagent for use.

[0027] ②Synthesis of 2,2'-bipyridine-4,4'-(5-hexyl-2-thiophene): 114g of 4,4'-dibromo-2,2'-bipyridine, 1,2 - bis(diphenylphosphine) ethane nickel chloride 6.8g, triphenylphosphine (P(Ph) 3 ) 342g, dimethylformamide (DMF) 1710g, slowly drop 450g of zinc reagent dropwise under nitrogen protection environment, react at 80°C for 1h and the reaction is complete, cool the product and filter, add 1170g of petroleum ether to the filter cake, stir, filter and dry , then add 1170g of dichloromethane to dissolve, add 11.7g of activated carbon for decolorization and filtration, wash the filter cake with 250g of dichloromethane, evaporate the filtrate to dryness and recrystallize (ethyl acetate:petroleum ether=1:5) to obtain 2,2'-linked Pyridine-4,4'-(5-hexyl-...

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Abstract

The invention discloses a method for preparing 2,2'-bipyridyl-4,4-(5-hexyl-2-thiophene), and belongs to the field of organic synthesis. The method comprises the following steps: 1, reacting zinc chloride, tetrahydrofuran and a grignard reagent to prepare a zinc reagent for later use; 2, reacting 4,4-dibromo-2,2-bipyridyl with the zinc reagent under a catalytic system comprising 1,2-bis(diphenylphosphino)ethane nickel chloride, triphenylphosphine and dimethyl formamide in a nitrogen protective environment, and performing cooling, filtering, washing, recrystallizing and the like to refine an obtained product to obtain a 2,2'-bipyridyl-4,4-(5-hexyl-2-thiophene) product. According to the method, the raw materials are low in cost, a generated intermediate is nontoxic, the reaction process is easy to control, the environment pollution is less, and the method has high industrial value.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and specifically relates to a method for preparing 2,2'-bipyridine-4,4'-(5-hexyl-2-thiophene). Background technique [0002] 2,2'-Bipyridyl and its derivatives are an important class of chemical and pharmaceutical synthesis intermediates. They have a unique chelation effect and can react with many metal ions to form metal complexes. They are widely used in the coordination of metal catalysts. Phosphors, luminescent materials, pharmaceutical intermediates, and photosensitizers and many other fields. 2,2'-bipyridine-4,4'-(5-hexyl-2-thiophene) is a 2,2'-bipyridine derivative substituted at the 4,4' position, which can be used as a ligand for various metal catalysts use has aroused great concern. [0003] The earliest method for synthesizing bipyridine derivatives was the Ullman reaction, and then Suzuki reported the Sunuki-Miyaura reaction in 1979, which used palladium as a catalyst and coupled ha...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D409/14
CPCC07D409/14
Inventor 胡孝伦王建莉杨勇石田丽徐亚娟
Owner 上海惠仁(夏邑)制药有限公司
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