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Preparation method of bromo-substituted benzimidazole derivative

A technology of benzimidazole and derivatives, applied in the field of novel preparation of pharmaceutical intermediates, can solve problems such as difficulty in synthesis

Inactive Publication Date: 2015-02-25
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 5-bromo-1,6-dimethyl-1H-benzo[d]imidazole-2-carbaldehyde is difficult at present

Method used

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  • Preparation method of bromo-substituted benzimidazole derivative
  • Preparation method of bromo-substituted benzimidazole derivative
  • Preparation method of bromo-substituted benzimidazole derivative

Examples

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Embodiment 1

[0022] (1) Synthesis of 4-bromo-5-methyl-1,2-phenylenediamine

[0023] Add 36g of 5-bromo-4-methyl-2-nitroaniline to 400ml of ethanol, add 3g of 10% palladium carbon, feed hydrogen, stir overnight, filter, collect the filtrate, concentrate to obtain 27g of 4-bromo-5 -Methyl-1,2-phenylenediamine.

[0024] (2) Synthesis of 5-bromo-2-(diethoxymethyl)-6-methyl-1H-benzo[d]imidazole

[0025] Add 28g of 4-bromo-5-methyl-1,2-phenylenediamine to 350ml of absolute ethanol, add 17g of sodium ethoxide, then add 32g of ethyl 2,2-diethoxyacetate, heat and reflux for 24 hours , cooled, concentrated, added water and ethyl acetate for extraction and separation, collected the organic phase, dried, and concentrated to obtain 19g of 5-bromo-2-(diethoxymethyl)-6-methyl-1H-benzo[ d] imidazole.

[0026] (3) Synthesis of 5-bromo-2-(diethoxymethyl)-1,6-dimethyl-1H-benzo[d]imidazole

[0027] 19g of 5-bromo-2-(diethoxymethyl)-6-methyl-1H-benzo[d]imidazole was added to 150ml of N,N-dimethylformamide,...

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Abstract

The invention discloses a preparation method of a bromo-substituted benzimidazole derivative 5-bromo-1,6-dimethyl-1H-benzo[d]imidazolyl-2-formaldehyde, which comprises the following steps: by using 5-bromo-4-methyl-2-nitroaniline as the initial raw material, carrying out reduction, cyclization, methylation and hydrolysis reaction to obtain the target product. The compound is an important drug intermediate.

Description

technical field [0001] The present invention relates to a novel preparation method of a pharmaceutical intermediate, in particular to the preparation of a bromine-substituted benzimidazole derivative 5-bromo-1,6-dimethyl-1H-benzo[d]imidazole-2-carbaldehyde method. technical background [0002] The compound 5-bromo-1,6-dimethyl-1H-benzo[d]imidazole-2-carbaldehyde has the structural formula: [0003] [0004] The compound 5-bromo-1,6-dimethyl-1H-benzo[d]imidazole-2-carbaldehyde and related derivatives are widely used in medicinal chemistry and organic synthesis. Currently, the synthesis of 5-bromo-1,6-dimethyl-1H-benzo[d]imidazole-2-carbaldehyde 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 bromine-substituted benzimidazole derivative 5-bromo-1,6-dimethyl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/12
CPCC07D235/12
Inventor 陈芳军李书耘
Owner 湖南华腾制药有限公司
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