Preparation method of 6-bromoindole derivative

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

Inactive Publication Date: 2015-01-21
湖南华腾制药有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The synthesis of tert-butyl 2-(6-bromo-1H-...

Method used

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  • Preparation method of 6-bromoindole derivative
  • Preparation method of 6-bromoindole derivative
  • Preparation method of 6-bromoindole derivative

Examples

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Embodiment 1

[0022] (1) Synthesis of 2-(6-bromo-1H-indol-3-yl)-2-oxoacetyl chloride

[0023] Add 40g of 6-bromoindole to 450ml of anhydrous dichloromethane, add 15g of aluminum trichloride, then add 60g of oxalyl chloride, heat to reflux for 2 hours, cool to room temperature, then add water, separate, dry, concentrate, The residue was subjected to column separation to obtain 47 g of 2-(6-bromo-1H-indol-3-yl)-2-oxoacetyl chloride.

[0024] (2) Synthesis of 2-(6-bromo-1H-indol-3-yl)-2-oxoacetamide

[0025] Add 45g of 2-(6-bromo-1H-indol-3-yl)-2-oxoacetyl chloride to a mixture of 100ml of water and 500ml of ammonia water, stir at room temperature for 4 hours, add ethyl acetate for extraction, separate liquids and dry , concentrated, and the residue was separated on a silica gel column to obtain 32 g of 2-(6-bromo-1H-indol-3-yl)-2-oxoacetamide.

[0026] (3) Synthesis of 2-(6-bromo-1H-indol-3-yl)ethylamine

[0027] Add 30g of 2-(6-bromo-1H-indol-3-yl)-2-oxoacetamide into 200ml of anhydrous t...

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Abstract

The invention discloses a preparation method of a 6-bromoindole derivative: tertiary butyl 2-(6-bromo-1H-indole-3-yl) ethyl carbamic acid. The preparation method comprises the following steps: by using 6-bromoindole as an initial raw material, carrying out Friedel-Craft reaction; carrying out amidation; reducing; and carrying out t-butyloxycarboryl protective reaction to obtain the target product. The compound is an important medical intermediate.

Description

technical field [0001] The present invention relates to a novel preparation method of a pharmaceutical intermediate, in particular to a preparation method of 6-bromoindole derivative tert-butyl 2-(6-bromo-1H-indol-3-yl)ethyl carbamic acid . technical background [0002] Compound tert-butyl 2-(6-bromo-1H-indol-3-yl)ethylcarbamate, the structural formula is: [0003] NBoc [0004] The present compound tert-butyl 2-(6-bromo-1H-indol-3-yl)ethylcarbamate and related derivatives are widely used in medicinal chemistry and organic synthesis. Currently, the synthesis of tert-butyl 2-(6-bromo-1H-indol-3-yl)ethylcarbamate 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 method for preparing tert-butyl 2-(6-bromo-1H-indol-3-yl)ethyl carbamic acid, which uses 6-bromoindole as the starting m...

Claims

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Application Information

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IPC IPC(8): C07D209/16
CPCC07D209/16C07D209/18
Inventor 陈芳军李书耘
Owner 湖南华腾制药有限公司
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