Synthesis method of pyridine derivative 2-tert-butoxy-6-methylene chloropyridine

A technology of methylenechloropyridine and tert-butoxypyridine, which is applied in the field of synthesis of pyridine derivatives, can solve the problems of high reaction temperature, poisonous catalyst, and easy failure, and achieve high reactivity and few reaction steps , the effect of short reaction time

Inactive Publication Date: 2015-04-08
HARBIN INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are disadvantages such as too high reaction temperature or poisonous catalysts. Even if environmentally friendly catalysts such as phosphine, mercaptans and amines are selected, there are catalysts that are sensitive and easy to fail, low yield, no regioselectivity, and product structure. uncontrollable issues

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  • Synthesis method of pyridine derivative 2-tert-butoxy-6-methylene chloropyridine
  • Synthesis method of pyridine derivative 2-tert-butoxy-6-methylene chloropyridine
  • Synthesis method of pyridine derivative 2-tert-butoxy-6-methylene chloropyridine

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Embodiment 1

[0020] This example provides a synthetic method of pyridine derivative 2-tert-butoxy-6-methylenechloropyridine, the specific synthetic steps are as follows:

[0021] 1. In N 2 Under protection, add 7.0g (0.03mol) of 2-bromo-6-tert-butoxypyridine to the three-necked flask, add 100ml of toluene as a solvent, and add 12ml of n-butyllithium dropwise at -78°C (M=2.5mol / L) . After stirring at low temperature for 30 minutes, the system solution gradually changed from light yellow to orange yellow. At the above temperature, 4.4 g (0.06 mol) of N,N-dimethylformamide (DMF) was added and reacted at 0°C for 45 min, the color of the reaction solution system became light and yellow. After the reaction was completed, the liquid was extracted and separated with ethyl acetate. After drying and standing still, 6.0 g of the crude product 2-tert-butoxy-6-pyridinal was obtained by suspension evaporation, which was directly used for feeding in the next step. The reaction equation is as follo...

Embodiment 2

[0028] This example provides a synthetic method of pyridine derivative 2-tert-butoxy-6-methylenechloropyridine, the specific synthetic steps are as follows:

[0029] 1. In N 2 Under protection, add 7.0g (0.03mol) of 2-bromo-6-tert-butoxypyridine to the three-necked flask, add 100ml of toluene as a solvent, and add 12ml of n-butyllithium dropwise at -78°C (M=2.5mol / L) . After stirring at low temperature for 30 minutes, the system solution gradually changed from light yellow to orange yellow. At the above temperature, 4.4 g (0.06 mol) of N,N-dimethylformamide (DMF) was added and reacted at 0°C for 45 min, the color of the reaction solution system became light and yellow. After the reaction was completed, the liquid was extracted and separated with ethyl acetate. After drying and standing still, 6.0 g of the crude product 2-tert-butoxy-6-pyridinal was obtained by suspension evaporation, which was directly used for feeding in the next step. The reaction equation is as ...

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Abstract

The invention discloses a synthesis method of a pyridine derivative 2-tert-butoxy-6-methylene chloropyridine. The synthesis method of the pyridine derivative 2-tert-butoxy-6-methylene chloropyridine comprises the following steps: carrying out reaction on low-cost 2-bromo-6-tert-butoxy pyridine taken as a raw material as well as n-butyl lithium and DMF (dimethyl formamide) sequentially in presence of N2 and at low temperature, thus preparing a pyridine aldehyde compound; reducing aldehyde to obtain alcohol in a corresponding structure by utilizing sodium borohydride or lithium aluminium hydride as a reducing agent; and replacing hydroxyl in alcohol by utilizing a chlorine atom, thus obtaining a pyridine derivative containing methylene chloride and tert-butoxy groups with relatively high activity. The synthesis method of the pyridine derivative 2-tert-butoxy-6-methylene chloropyridine has the advantages that overall reaction steps are less, the reaction time is short, and the yield is high; and the prepared 2-tert-butoxy-6-methylene chloropyridine is easy to coordinate with a metal atom or other atoms and can be taken as a pyridine derivative ligand to be coordinated with metal, so as to prepare an organic metal catalyst or be applied to synthesis of a pyridine derivative drug.

Description

technical field [0001] The invention relates to a synthesis process of pyridine derivative compounds, in particular to a synthesis method of pyridine derivative 2-tert-butoxy-6-methylenechloropyridine. Background technique [0002] The study of pyridine and its derivatives involves many fields of chemistry. In coordination chemistry, monocyclic pyridine, bipyridine, terpyridine, etc. are easy to provide nitrogen atoms to coordinate with metals to prepare efficient organometallic catalysts. Pyridine derivatives are also used in emerging fields such as the preparation of functional materials, characteristic surfaces, and the synthesis of supramolecules and polymers. The synthesis of pyridine and its derivatives is more important that it is some natural products with specific biological activities, such as vitamin B 6 , nicotine, coenzymes, alkaloids and other important components in the structure. In particular, it occupies an important position in medicinal chemistry. A la...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/64B01J31/22
CPCC07D213/64
Inventor 胡博文崔文石靖龚大伟陈大发
Owner HARBIN INST OF TECH
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