Chemical synthesis method for (E)-4-styryl pyridine

A technology of styrylpyridine and vinylpyridine, which is applied in the field of chemical synthesis of -4-styrylpyridine, can solve the problems of limited promotion, harsh reaction conditions, low selectivity and yield of E-configuration products, and achieve The effect of advanced and reasonable process route, mild reaction conditions, great implementation value and social and economic benefits

Inactive Publication Date: 2013-09-18
WENZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, both methods use halogen-containing aromatic hydrocarbons as substrates, which are seriously polluting to the environment.
Another method is the reaction of 4-picoline with benzaldehyde (such as Dalton Transactions, (9), 1376-1385; 2004), which uses a strong base lithium diisopropylamide (LDA), and the reaction conditions are harsh , and the selectivity and yield of the resulting E-configuration product are very low
Therefore, the generalization of these methods mentioned above is limited

Method used

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  • Chemical synthesis method for (E)-4-styryl pyridine
  • Chemical synthesis method for (E)-4-styryl pyridine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] The amount ratio of feed material 4-vinylpyridine: phenylboronic acid: palladium catalyst: oxidizing agent: basic compound is 1.0: 1.0: 0.05: 0.05: 2.0 Feeding, 4-vinylpyridine 21.0g (0.2mol); Phenylboronic acid 24.4g (0.2mol); The palladium catalyst is di(acetylacetonate) palladium, and the feeding quality is 3.04g (0.01mol); the oxidizing agent is copper acetate monohydrate, and the feeding quality is 1.99g (0.01mol); the basic compound is sodium bicarbonate, and the feeding quality 33.6g (0.4mol); the organic solvent is 210g of N,N'-dimethylformamide, the total amount of which is 10 times the mass of 4-vinylpyridine.

[0027] Dissolve phenylboronic acid, palladium catalyst, oxidant and basic compound in an organic solvent (the amount of the organic solvent used is 6 times the mass of 4-vinylpyridine). Dissolve 4-vinylpyridine in an organic solvent (the amount of organic solvent is 4 times the mass of 4-vinylpyridine), slowly add dropwise to the above solution of phen...

Embodiment 2

[0032] The amount ratio of feed material 4-vinylpyridine: phenylboronic acid: palladium catalyst: oxidizing agent: basic compound is 1.0: 1.5: 0.05: 0.05: 2.0 Feeding, 4-vinylpyridine 21.0g (0.2mol); Phenylboronic acid 36.6g (0.3mol); The palladium catalyst is di(acetylacetonate) palladium, and the feeding quality is 3.04g (0.01mol); the oxidant is copper acetate monohydrate, and the feeding quality is 1.99g (0.01mol); the basic compound is sodium bicarbonate, and the feeding quality 33.6g (0.4mol); the organic solvent is 210g of N,N'-dimethylformamide, the total amount of which is 10 times the mass of 4-vinylpyridine.

[0033] The reaction temperature was 90°C, the reaction time was 24 hours, and other operations were the same as in Example 1. (E)-4-Styrylpyridine was 26.4g, the yield was 73%, and the purity was 98.5%.

Embodiment 3

[0035] The amount ratio of feed material 4-vinylpyridine: phenylboronic acid: palladium catalyst: oxidizing agent: basic compound is 1.0: 2.0: 0.05: 0.1: 3.0 feeding, 4-vinylpyridine 21.0g (0.2mol); Phenylboronic acid 48.8g (0.4mol); The palladium catalyst is di(acetylacetonate) palladium, and the feeding quality is 3.04g (0.01mol); the oxidant is copper acetate monohydrate, and the feeding quality is 3.98g (0.02mol); the basic compound is sodium bicarbonate, and the feeding quality 50.4g (0.6mol); the organic solvent is 210g of N,N'-dimethylformamide, the total amount of which is 10 times the mass of 4-vinylpyridine.

[0036] The reaction temperature is 90°C, the reaction time is 36 hours, other operations are the same as in Example 1, (E)-4-styrylpyridine is 27.5g, the yield is 76%, and the purity is 98.2%.

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Abstract

The invention discloses a chemical synthesis method for (E)-4-styryl pyridine, which comprises the following steps of: fully reacting 4-vinylpyridine and phenylboric acid serving as raw materials in the presence of a palladium catalyst, an oxidant and an alkaline compound in an inert organic solvent, and separating and purifying reaction liquid after reaction is finished to obtain the (E)-4-styryl pyridine. By the synthesis method, reactants are environment-friendly, reaction selectivity and reaction yield are high, the process is advanced and reasonable, and reaction conditions are mild, so high implementation value and social and economic benefits are achieved.

Description

(1) Technical field [0001] The invention relates to a chemical synthesis method of (E)-4-styrylpyridine. (2) Background technology [0002] (E)-4-Styrylpyridine is an important monodentate ligand and a key intermediate widely used in drug synthesis. Recent studies have shown that this type of compound plays an important role in materials science. [0003] In the prior art, it is more common to pass 4-vinylpyridine and iodobenzene (such as: Journal of Molecular Catalysis A: Chemical, 2010, 332 (1-2), 70-75) or bromobenzene (such as: Chemistry- -A European Journal, 2008, 14(26), 7969-7977) coupling reaction to synthesize (E)-4-styrylpyridine. However, both methods use halogen-containing aromatic hydrocarbons as substrates, which are seriously polluting to the environment. Another method is the reaction of 4-picoline with benzaldehyde (such as Dalton Transactions, (9), 1376-1385; 2004), which uses a strong base lithium diisopropylamide (LDA), and the reaction conditions are ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/16C07D213/127
Inventor 吴华悦陈久喜刘妙昌高文霞黄小波
Owner WENZHOU UNIV
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