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Preparation method of 1,1'-dimethyl-2,2'-diketone-4,4'-dipyridyl

A kind of methyl pyridine and dimethyl technology, applied in the field of organic synthesis, can solve the problem that the synthesis method cannot be universal, and achieve the effects of improving the utilization rate of workshop equipment, simple reaction system and simple preparation process

Inactive Publication Date: 2019-05-14
SHANXI MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are certain differences in structure between 2,2'-bipyridine derivatives and 4,4'-bipyridine derivatives, and the synthesis methods of the two cannot be used universally, so it is still necessary to find a new synthesis method for 4 , Synthesis of 4′-bipyridine derivatives

Method used

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  • Preparation method of 1,1'-dimethyl-2,2'-diketone-4,4'-dipyridyl
  • Preparation method of 1,1'-dimethyl-2,2'-diketone-4,4'-dipyridyl
  • Preparation method of 1,1'-dimethyl-2,2'-diketone-4,4'-dipyridyl

Examples

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Embodiment 1

[0026] A preparation method of 1,1'-dimethyl-2,2'-diketone-4,4'-bipyridine, comprising the following steps:

[0027] (1) Dissolve 18.6g of 4-bromo-1-methylpyridin-2-one in 250 mL of DMSO, stir well, then add 14.8g of potassium acetate, 30.5g of pinacol diborate and 7.0g of Pd( dppf) 2 Cl 2 , under the protection of nitrogen, reflux at 80°C overnight, TLC point plate to detect the reaction end point, then the reaction solution flows through the silica gel column for separation, and the column is rinsed with a mixed solution of methanol and dichloromethane with a volume ratio of 1:10 to collect the target The product was evaporated to dryness with a rotary evaporator to remove the organic solvent to obtain 9.0 g of compound I.

[0028] (2) 7.05g of compound I obtained in step (1) and 6.2g of 4-bromo-1-methylpyridin-2-one, 6.3g of sodium carbonate and 2.4g of tetrakistriphenylphosphine palladium dichloride were successively dissolved in 200mL Dioxane and 40mL water were stirre...

Embodiment 2

[0032] A preparation method of 1,1'-dimethyl-2,2'-diketone-4,4'-bipyridine, comprising the following steps:

[0033] (1) Dissolve 18.2g of 4-bromo-1-methylpyridin-2-one in 260 mL of DMSO, stir well, then add 14.1g of potassium acetate, 30.2g of pinacol diborate and 7.2g of Pd( dppf) 2 Cl 2 , under the protection of nitrogen, reflux at 90°C overnight, TLC point plate to detect the reaction end point, then the reaction solution flows through the silica gel column for separation, and the column is rinsed with a mixed solution of methanol and dichloromethane with a volume ratio of 1:5 to collect the target The product was evaporated to dryness with a rotary evaporator to remove the organic solvent to obtain 9.1 g of compound I.

[0034] (2) 7.5g of compound I obtained in step (1) and 6.5g of 4-bromo-1-methylpyridin-2-one, 6.2g of sodium carbonate and 2.5g of tetrakistriphenylphosphine palladium dichloride were dissolved in 210mL successively Dioxane and 50mL water were stirred ...

Embodiment 3

[0038] A preparation method of 1,1'-dimethyl-2,2'-diketone-4,4'-bipyridine, comprising the following steps:

[0039] (1) Dissolve 17.8g of 4-bromo-1-methylpyridin-2-one in 240 mL of DMSO, stir well, then add 13.9g of potassium acetate, 30.1g of biboronic acid pinacol ester and 7.8g of Pd( dppf) 2 Cl 2 , under the protection of nitrogen, reflux at 100°C overnight, TLC point plate to detect the reaction end point, then the reaction solution flows through the silica gel column for separation, and the column is rinsed with a mixed solution of methanol and dichloromethane with a volume ratio of 2:5 to collect the target The product was evaporated to dryness with a rotary evaporator to remove the organic solvent to obtain 9.3 g of compound I.

[0040] (2) 7.8g of compound I obtained in step (1) and 6.6g of 4-bromo-1-methylpyridin-2-one, 6.8g of sodium carbonate and 2.7g of tetrakistriphenylphosphine palladium dichloride were successively dissolved in 200mL Dioxane and 50mL water ...

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PUM

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Abstract

The invention discloses a preparation method of 1,1'-dimethyl-2,2'-diketone-4,4'-dipyridyl, the preparation method comprises the following steps: (1) dissolving 4-bromine-1-methylpyridine-2-ketone into DMSO (dimethylsulfoxide), evenly stirring, sequentially adding potassium acetate, bisdiboron and Pd(dppf)2Cl2, backflowing overnight under the protection of nitrogen, detecting the reaction endpointthrough a TLC (Thin-Layer Chromatography) point plate, and post-processing to obtain the 1,1'-dimethyl-2,2'-diketone-4,4'-dipyridyl. The raw materials in the method are simple and easy to get, the reaction steps are fewer, the product yield is higher, and the preparation method is suitable for large-scale industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a preparation method of 1,1'-dimethyl-2,2'-diketone-4,4'-bipyridine. Background technique [0002] Nowadays, electron-deficient six-membered heterocyclic compounds are a very important class of organic compounds, among which nitrogen-containing heterocyclic compounds, such as pyridine and pyridine derivatives, are an important class. Nitrogen-containing heterocyclic compounds are often used as structural units of medicines and pesticides due to their high water solubility, stable structure, unique biological activity, low toxicity and high systemic property, and are widely used in medicine, pesticides, dyes and rubber Products and other industrial fields. In addition, nitrogen-containing heterocyclic compounds, as π-electron conjugated heterocyclic and rigid planar compounds, have strong fluorescence effects and can be used in dyes and solar cells. As a new...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/64
Inventor 贠克明王显连马红娟王颖路玉平尉志文苏红亮张潮贾娟王乐乐王锐利
Owner SHANXI MEDICAL UNIV
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