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Preparation method of bromobenzo[d]oxazole derivative

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

Inactive Publication Date: 2015-02-04
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 1-(5-bromobenzo[d]oxazol-2-yl)piperidine-4-carboxylic acid is difficult at present

Method used

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  • Preparation method of bromobenzo[d]oxazole derivative
  • Preparation method of bromobenzo[d]oxazole derivative
  • Preparation method of bromobenzo[d]oxazole derivative

Examples

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Embodiment 1

[0022] (1) Synthesis of potassium 5-bromobenzo[d]oxazole-2-thiolate

[0023] Add 25g of 2-amino-4-bromophenol and 37g of potassium ethyl xanthate to 300ml of pyridine, heat and reflux and stir for 12 hours, cool, concentrate, add 10% hydrochloric acid, then add ethyl acetate, extract and separate, collect The organic phase was dried and concentrated to yield 19 g of potassium 5-bromobenzo[d]oxazole-2-thiolate.

[0024] (2) Synthesis of 5-bromo-2-chlorobenzo[d]oxazole

[0025] Add 18g of 5-bromobenzo[d]oxazole-2-potassium thiolate into 100ml of thionyl chloride, heat and reflux and stir for 4 hours, cool to room temperature, and concentrate to obtain 13g of 5-bromo-2-chlorobenzo [d] Oxazole.

[0026] (3) Synthesis of ethyl 1-(5-bromobenzo[d]oxazol-2-yl)piperidine-4-carboxylate

[0027] Add 12g of 5-bromo-2-chlorobenzo[d]oxazole and 16g of methyl 4-piperidinecarboxylate into 150ml of N,N-dimethylformamide, add 20g of potassium carbonate, heat and reflux and stir for 22 hours,...

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Abstract

The invention discloses a preparation method of bromobenzo[d]oxazole derivative 1-(5-bromobenzo[d]oxazol-2-yl)piperidine-4-carboxylic acid. 2-amino-4-bromophenol as a starting material is subjected to ring-closing reaction, chlorination, condensation and hydrolysis to obtain the target product. The compound is an important medicinal intermediate.

Description

technical field [0001] The present invention relates to a novel preparation method of a pharmaceutical intermediate, in particular to a bromobenzo[d]oxazole derivative 1-(5-bromobenzo[d]oxazol-2-yl)piperidine-4- Methods for the preparation of carboxylic acids. technical background [0002] Compound 1-(5-bromobenzo[d]oxazol-2-yl)piperidine-4-carboxylic acid, the structural formula is: [0003] [0004] The present compound 1-(5-bromobenzo[d]oxazol-2-yl)piperidine-4-carboxylic acid and related derivatives are widely used in medicinal chemistry and organic synthesis. Currently, the synthesis of 1-(5-bromobenzo[d]oxazol-2-yl)piperidine-4-carboxylic acid 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 bromobenzo[d]oxazole derivative 1-(5-bromobenzo[d]oxazol-2-...

Claims

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Application Information

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IPC IPC(8): C07D413/04
CPCC07D413/04
Inventor 李书耘
Owner 湖南华腾制药有限公司
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