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Preparation method of 6-bromo pyran derivative

A technology of bromopyran derivatives and pyran, which is applied in the field of new preparation of pharmaceutical intermediates, and can solve problems such as difficult synthesis

Inactive Publication Date: 2015-08-12
湖南华腾制药有限公司
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  • Description
  • Claims
  • Application Information

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Problems solved by technology

The synthesis of 6-bromo-N-methyl-3,4-dihydro-2H-pyran-3-amine is difficult at present

Method used

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  • Preparation method of 6-bromo pyran derivative
  • Preparation method of 6-bromo pyran derivative
  • Preparation method of 6-bromo pyran derivative

Examples

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Embodiment 1

[0022] (1) Synthesis of 2-(5-bromo-2-phenoxy ethyl acetate) ethyl acetate

[0023] Add 15g of methyl 2-(5-bromo-2-hydroxyphenyl)acetate to 120ml of N,N-dimethylformamide, add 14g of ethyl bromoacetate and 11g of potassium carbonate, heat and stir to reflux, and cool to room temperature , adding water and ethyl acetate, extracting and separating the layers, collecting the organic phase, drying, and concentrating to obtain 9g of 2-(5-bromo-2-phenoxy ethyl acetate) ethyl acetate.

[0024] (2) Synthesis of ethyl 6-bromo-3-oxo-3,4-dihydro-2H-chromene-4-carboxylate

[0025] Add 9g of 2-(5-bromo-2-phenoxyethyl acetate) ethyl acetate to 60ml of ethanol, cool down to 0°C, add 8g of sodium ethoxide, heat and stir under reflux for 3 hours, cool to room temperature, concentrate, add Extraction and separation with water and ethyl acetate, the organic phase was collected, dried, and concentrated to obtain 6 g of ethyl 6-bromo-3-oxo-3,4-dihydro-2H-chromene-4-carboxylate.

[0026] (3) Synth...

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Abstract

The invention discloses a preparation method of a 6-bromo pyran derivative, 6-bromo-N-methyl-3,4-dihydro-2H-pyran-3-amine. A starting material 2-(5-bromo-2-hydroxyphenyl) methyl acetate is subjected to etherification, cyclization, decarboxylation and amination reduction to obtain an object product. The product of the invention can be used as a template micromolecule to synthesize a variety of chemical libraries.

Description

technical field [0001] The present invention relates to a novel preparation method of a pharmaceutical intermediate, in particular to the preparation of a 6-bromopyran derivative 6-bromo-N-methyl-3,4-dihydro-2H-pyran-3-amine method. technical background [0002] Compound 6-bromo-N-methyl-3,4-dihydro-2H-pyran-3-amine, the structural formula is: [0003] [0004] The compound 6-bromo-N-methyl-3,4-dihydro-2H-pyran-3-amine and related derivatives are widely used in medicinal chemistry and organic synthesis. Currently, the synthesis of 6-bromo-N-methyl-3,4-dihydro-2H-pyran-3-amine is difficult. Therefore, it is necessary to develop a synthetic method with easy-to-obtain raw materials, convenient operation, easy-to-control reaction and suitable overall yield. Contents of the invention [0005] The invention discloses a preparation method of a 6-bromopyran derivative 6-bromo-N-methyl-3,4-dihydro-2H-pyran-3-amine, which uses 2-(5-bromo-2 -Hydroxyphenyl) methyl acetate is th...

Claims

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Application Information

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IPC IPC(8): C07D311/58
CPCC07D311/04
Inventor 不公告发明人
Owner 湖南华腾制药有限公司
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