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Preparation method of 2-(2-alkylphenoxy)pyridine derivative

A technology of alkylphenoxy and phenoxypyridine, applied in the field of chemistry, can solve the problems of difficult separation, high cost, difficult target product, etc., and achieve the effect of low cost, simple process and good specificity

Inactive Publication Date: 2017-08-15
ANYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Although the method is mature and reliable, there are a large amount of para-alkylphenoxypyridine and a small amount of meta-alkylphenoxypyridine in the reaction process, which leads to a decline in the yield of the target product; and these byproducts are structurally similar to the target product, The molecular weight is the same, it is particularly difficult to separate, and it is difficult to obtain high-purity target products, and the cost is high

Method used

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  • Preparation method of 2-(2-alkylphenoxy)pyridine derivative
  • Preparation method of 2-(2-alkylphenoxy)pyridine derivative
  • Preparation method of 2-(2-alkylphenoxy)pyridine derivative

Examples

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Embodiment 1

[0012] Add 40 mg (0.2 mmol) 2-(4-methoxyphenoxy) pyridine, 98 mg (0.6 mmol) 1-bromo-n-hexane, 6 mg (0.01 mmol) dichlorobis(4-methanol) into a 20 mL pressure-resistant reaction tube Isopropylphenyl) ruthenium, 55mg (0.4mmol) potassium carbonate, 11mg (0.06mmol) 1-adamantanecarboxylic acid, 1.5mL benzene, sealed under nitrogen, heated to 120 ° C, stirred for 24 hours, after the reaction, After separation by column chromatography, 38 mg of the target product 2-(2-n-hexyl-4-methoxyphenoxy)pyridine was obtained with a yield of 67%.

Embodiment 2

[0014] Add 37 mg (0.2 mmol) 2-(4-methylphenoxy) pyridine, 92 mg (0.6 mmol) 1-bromo-3-methoxypropane, 6 mg (0.01 mmol) dichlorobis (4-Methylisopropylphenyl)ruthenium, 55mg (0.4mmol) potassium carbonate, 11mg (0.06mmol) 1-adamantanecarboxylic acid, 1.5mL benzene, sealed under nitrogen, heated to 120°C for reaction, stirred for 24 hours , after the reaction, separated by column chromatography to obtain 31 mg of the target product 2-(4-methyl-2-(3-methoxypropyl)phenoxy)pyridine with a yield of 60%.

Embodiment 3

[0016] Add 34mg (0.2mmol) 2-phenoxypyridine, 117mg (0.6 mmol) ethyl 4-bromobutyrate, 6mg (0.01mmol) dichlorobis(4-methylisopropylbenzene) into a 20mL pressure-resistant reaction tube base) ruthenium, 55mg (0.4mmol) potassium carbonate, 11mg (0.06mmol) 1-adamantanecarboxylic acid, 1.5mL benzene, sealed under nitrogen, heated to 120°C for reaction, stirred for 24 hours, after reaction, separated by column chromatography to obtain The target product 4-(2-(2-pyridyloxy)ethyl phenylbutyrate was 35mg, and the yield was 62%.

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Abstract

A preparation method of a 2-(2-alkylphenoxy)pyridine derivative adopts a reaction of a 2-phenoxypyridine derivative and a primary bromoalkane compound. The method concretely comprises the following steps: directly adding the 2-phenoxypyridine derivative, the primary bromoalkane compound, a catalyst, an additive, an alkali and a solvent into a reaction device, stirring and heating the above added substances until the temperature is 90-130 DEG C, carrying out a reaction for 18-36 h, and separating the obtained product to obtain the 2-(2-alkylphenoxy)pyridine derivative, wherein the catalyst is dichloro(p-cymene)ruthenium dimer; the alkali is potassium carbonate or lithium carbonate; the additive is 1-adamantanecarboxylic acid or naphthenic acid; and the solvent is benzene or DMF or ethylene glycol dimethyl ether. The method has the advantages of easiness in obtaining of synthesis raw materials, simple process, and very good specificity of the reaction.

Description

technical field [0001] The invention relates to a preparation method of pyridine derivatives, in particular to a method for synthesizing 2-(2-alkylphenoxy)pyridine derivatives, belonging to the field of chemistry. Background technique [0002] 2-(2-Alkylphenoxy)pyridine and its derivatives are an important molecular skeleton, which widely exists in natural products and compounds with biological activity. The usual synthesis method of this type of compound is: phenoxypyridine and bromoalkane are obtained by electrophilic substitution reaction, and the reaction formula is as follows: [0003] [0004] Although the method is mature and reliable, there are a large amount of para-alkylphenoxypyridine and a small amount of meta-alkylphenoxypyridine in the reaction process, which leads to a decline in the yield of the target product; and these byproducts are structurally similar to the target product, With the same molecular weight, it is particularly difficult to separate, and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/643
CPCC07D213/643
Inventor 李刚杨素玲许志宪黄东风袁琳朱彪
Owner ANYANG NORMAL UNIV
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