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Method for preparing vilazodone intermediate and vilazodone drug by using cheap metal copper

A technology for vilazodone and intermediates, which is applied in the field of preparing vilazodone medicines, can solve the problems of difficult post-processing, long routes, and high preparation costs, and achieves good product purity and content, high atom economy, and good purity. Effect

Active Publication Date: 2019-08-06
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are long routes, difficult post-processing, high preparation costs, and certain risks in the synthesis of some intermediates

Method used

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  • Method for preparing vilazodone intermediate and vilazodone drug by using cheap metal copper
  • Method for preparing vilazodone intermediate and vilazodone drug by using cheap metal copper
  • Method for preparing vilazodone intermediate and vilazodone drug by using cheap metal copper

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0077] Example 1: Add ethyl 5-iodobenzofurancarboxylate (15.8g, 0.05mol), lithium hydroxide (5.99g, 0.25mol) and ammonia water (35.0g, 1.0mol) into a 500mL single-necked bottle, and stir at 50°C After 2 hours, TLC monitored the end point of the reaction, suction filtered, washed with water, and dried to obtain 13.6 g of white solid 5-iodobenzofuran-2-carboxamide, with a yield of 94.4% and a content of 99.5%. The data characterization of the 5-iodobenzofuran-2-carboxamide prepared in embodiment 1: 1 H NMR (400 MHz, CDCl 3 ):δ8.20(s,1H),8.00(d,1H),7.77(s,1H),7.59(m,2H),7.51(s,1H). 13 C NMR (100MHz, CDCl 3 ,ppm)δ159.00,152.74,150.15,129.15,129.05,124.90, 115.57,113.64,108.72.MS(ESI):240.0(100),242.0(98)([M+H] + ).

Embodiment 2

[0078] Example 2: Add ethyl 5-iodobenzofurancarboxylate (15.8g, 0.05mol), sodium hydroxide (10.0g, 0.25mol) and ammonia water (35.0g, 1.0mol) into a 500mL single-necked bottle, and stir at 50°C After 2 hours, TLC monitored the end point of the reaction, suction filtered, washed with water, and dried to obtain 14.0 g of white solid 5-iodobenzofuran-2-carboxamide, with a yield of 97.2%.

Embodiment 3

[0079] Example 3: Add ethyl 5-iodobenzofurancarboxylate (15.8g, 0.05mol), sodium methoxide (13.5g, 0.25mol) and ammonia water (35.0g, 1.0mol) into a 500mL single-necked bottle, and stir at room temperature for 2 hours , TLC to monitor the reaction end point, suction filtration, washing with water, and drying to obtain 13.5 g of white solid 5-iodobenzofuran-2-carboxamide, with a yield of 93.7%.

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Abstract

The invention discloses a method for preparing a vilazodone intermediate and a vilazodone drug by using cheap metal copper. The preparation method mainly takes 5- halobenzofurancarboxylic acid ethyl ester as an initial raw material to prepare the vilazodone intermediate 5-(piperazine-1-yl) benzofuran-2-carboxamide hydrochloride through amination reaction and Ullmann coupling reaction catalyzed bya cheap metal, and a high-purity vilazodone drug is further obtained from the vilazodone intermediate. The route has the advantages of high efficiency, low cost, high atom economy and good purity.

Description

technical field [0001] The invention relates to a method for preparing vilazodone intermediate and vilazodone by using cheap metal copper, in particular to the preparation of high-purity vilazodone intermediate 5-(piperazine) through Ullmann coupling reaction using cheap metal copper -1-yl)benzofuran-2-carboxamide hydrochloride and a method for further preparing vilazodone medicine using the intermediate. Background technique [0002] Vilazodone (Vilazodone), the chemical name is 5-[4-[4-(5-cyanindol-3-yl)butyl]piperazin-1-yl]benzofuran-2-carboxamide, The trade name is Viibryd. The US FDA approved Viibryd on January 21, 2011. The active ingredient is vilazodone hydrocholride (vilazodone hydrocholride) for the treatment of major depressive disorder in adults. Vilazodone is a 5-HT1A partial agonist and a selective 5-HT reuptake inhibitor (SSRI). Compared with existing clinical antidepressants, it has the characteristics of rapid onset of action and no adverse reactions to se...

Claims

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Application Information

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IPC IPC(8): C07D405/12
CPCC07D405/12
Inventor 翁意意杨婷苏为科
Owner ZHEJIANG UNIV OF TECH
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