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Preparation method of bromine-containing azide

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

Inactive Publication Date: 2015-11-18
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

Synthesis of 3-bromophenylazide compound 1-(3-azidopropyl)-3-bromo-4-ethoxybenzene is difficult at present

Method used

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  • Preparation method of bromine-containing azide
  • Preparation method of bromine-containing azide
  • Preparation method of bromine-containing azide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] (1) Synthesis of 3-(3-bromo-4-ethoxyphenyl)prop-2-en-1-ol

[0023] Add 16g of 3-(3-bromo-4-ethoxyphenyl)acrylic acid to 200ml of tetrahydrofuran, cool down to 0°C, slowly add 6g of lithium tetrahydrohydride in batches, stir at room temperature overnight, add water and ethyl acetate, and extract The liquid was separated, the organic phase was collected, dried and concentrated to obtain 7 g of 3-(3-bromo-4-ethoxyphenyl)prop-2-en-1-ol.

[0024] (2) Synthesis of 3-(3-bromo-4-ethoxyphenyl)propan-1-ol

[0025] Add 7g of 3-(3-bromo-4-ethoxyphenyl)prop-2-en-1-ol to 40ml of methanol, add 0.5g of 10% palladium carbon, pass in hydrogen, stir at room temperature overnight, filter, and collect the filtrate , concentrated to give 5 g of 3-(3-bromo-4-ethoxyphenyl)propan-1-ol.

[0026] (3) Synthesis of 3-(3-bromo-4-ethoxyphenyl)propyl methanesulfonate

[0027] Add 5g of 3-(3-bromo-4-ethoxyphenyl)propan-1-ol to 50ml of dibromomethane, add 3g of triethylamine, cool to 0°C, add 2.9g of...

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Abstract

The invention discloses a preparation method of 3-bromophenyl azide1-(3-azidopropyl)-3-bromo-4-ethoxybenzene. 3-(3-bromo-4-ethoxyphenyl)acrylic acid is used as a starting material, a target product 5 is obtained through reduction, hydrogenation, Ms (methylsulfonyl) loading and azidation reactions, and the product is used as a template micro-molecule for synthesis of various compound libraries.

Description

technical field [0001] The present invention relates to a novel preparation method of a pharmaceutical intermediate, in particular to a preparation method of a 3-bromophenyl azide compound 1-(3-azidopropyl)-3-bromo-4-ethoxybenzene . technical background [0002] Compound 1-(3-azidopropyl)-3-bromo-4-ethoxybenzene, the structural formula is: [0003] [0004] The present compound 3-bromophenyl azide compound 1-(3-azidopropyl)-3-bromo-4-ethoxybenzene and related derivatives are widely used in medicinal chemistry and organic synthesis. Currently, the synthesis of 3-bromophenyl azide compound 1-(3-azidopropyl)-3-bromo-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 preparation method of 3-bromophenyl azide compound 1-(3-azidopropyl)-3-bromo-4-ethoxybenzen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C247/10
Inventor 不公告发明人
Owner 湖南华腾制药有限公司