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Preparation method for aromatic azide

A technology of azide compounds and compounds, which is applied in the field of new synthesis of pharmaceutical intermediates, and can solve problems such as synthesis difficulties

Inactive Publication Date: 2015-12-16
湖南华腾制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthesis of aromatic azide compound 1-(3-azidopropyl)-3-chloro-4-ethoxybenzene is relatively difficult at present

Method used

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  • Preparation method for aromatic azide
  • Preparation method for aromatic azide
  • Preparation method for aromatic azide

Examples

Experimental program
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Effect test

Embodiment 1

[0022] (1) Synthesis of 3-(6-chloro-5-ethoxypyridin-2-yl)prop-2-en-1-ol

[0023] Add 16g of 3-(6-chloro-5-ethoxypyridin-2-yl)acrylic acid into 200ml of tetrahydrofuran, cool down to 0°C, slowly add 6g of lithium tetrahydrogen aluminum in batches, stir overnight at room temperature, add water and ethyl acetate ester, extraction and separation, the organic phase was collected, dried and concentrated to obtain 7g of 3-(6-chloro-5-ethoxypyridin-2-yl)prop-2-en-1-ol.

[0024] (2) Synthesis of 3-(6-chloro-5-ethoxypyridin-2-yl)propan-1-ol

[0025] Add 7g of 3-(6-chloro-5-ethoxypyridin-2-yl)prop-2-en-1-ol to 40ml of methanol, add 0.5g of 10% palladium carbon, feed hydrogen, stir overnight at room temperature, filter , the filtrate was collected and concentrated to give 5 g of 3-(6-chloro-5-ethoxypyridin-2-yl)propan-1-ol.

[0026] (3) Synthesis of 3-(6-chloro-5-ethoxypyridin-2-yl)propyl methanesulfonate

[0027] Add 5g of 3-(6-chloro-5-ethoxypyridin-2-yl)propan-1-ol into 50ml of dich...

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Abstract

The invention discloses a synthetic method for an aromatic azide: 6-(3-azido propyl)-2-chloro-3-ethoxypyridine. The synthetic method comprises: by taking 3-(6-chloro-5-ethoxypyridine-2-yl) acrylic acid as a starting raw material, carrying out reduction, hydrogenation, passing through Ms and azido reaction to obtain a target product 5. The product is used as template small molecules to synthesize diverse compound libraries.

Description

technical field [0001] The invention relates to a novel synthesis method of a pharmaceutical intermediate, in particular to a synthesis method of an aromatic azide compound 6-(3-azidopropyl)-2-chloro-3-ethoxypyridine. technical background [0002] Compound 6-(3-azidopropyl)-2-chloro-3-ethoxypyridine, the structural formula is: [0003] [0004] The compound aromatic azide compound 1-(3-azidopropyl)-3-chloro-4-ethoxybenzene and related derivatives are widely used in medicinal chemistry and organic synthesis. At present, the synthesis of aromatic azide compound 1-(3-azidopropyl)-3-chloro-4-ethoxybenzene is relatively 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 synthesis method of an aromatic azide compound 6-(3-azidopropyl)-2-chloro-3-ethoxypyridine, which uses 3-(6-chloro-5-eth...

Claims

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Application Information

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IPC IPC(8): C07D213/65
CPCC07D213/65
Inventor 不公告发明人
Owner 湖南华腾制药有限公司
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