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8-bromo pyran derivative preparation method

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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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthesis of 8-bromo-N-methyl-3,4-dihydro-2H-pyran-3-amine is difficult at present

Method used

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  • 8-bromo pyran derivative preparation method
  • 8-bromo pyran derivative preparation method
  • 8-bromo pyran derivative preparation method

Examples

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Embodiment 1

[0022] (1) Synthesis of 2-(3-bromo-2-phenoxy ethyl acetate) ethyl acetate

[0023] Add 12g of methyl 2-(3-bromo-2-hydroxyphenyl)acetate to 100ml of N,N-dimethylformamide, add 15g 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-(3-bromo-2-phenoxy ethyl acetate) ethyl acetate.

[0024] (2) Synthesis of ethyl 8-bromo-3-oxo-3,4-dihydro-2H-chromene-4-carboxylate

[0025] Add 9g of 2-(3-bromo-2-phenoxyethyl acetate) ethyl acetate to 40ml of ethanol, cool down to 0°C, add 7g 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 8-bromo-3-oxo-3,4-dihydro-2H-chromene-4-carboxylate.

[0026] (3) Synth...

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Abstract

The present invention discloses a preparation method of a 8-bromo pyran derivative 8-bromo-N-methyl-3,4-dihydro-2H-pyran-3-amine, wherein 2-(3-bromo-2-hydroxyphenyl)methyl acetate is adopted as a starting raw material and is subjected to reactions such as etherification, cyclization, decarboxylation, and ammoniation reduction to obtain the target product 5. According to the present invention, the product is used as template small molecules so as to synthesize a variety of compound libraries.

Description

technical field [0001] The present invention relates to a novel preparation method of a pharmaceutical intermediate, in particular to the preparation of 8-bromo-N-methyl-3,4-dihydro-2H-pyran-3-amine, a derivative of 8-bromopyran method. technical background [0002] Compound 8-bromo-N-methyl-3,4-dihydro-2H-pyran-3-amine, the structural formula is: [0003] [0004] The present compound 8-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 8-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 8-bromo-N-methyl-3,4-dihydro-2H-pyran-3-amine, an 8-bromopyran derivative. -Hydroxyphenyl) methyl acetate is the starting...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/04
CPCC07D311/04
Inventor 不公告发明人
Owner 湖南华腾制药有限公司