Yao Cheng
2012
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Journal
Journal of Nanjing University of Technology
Abstract
The compound(1-(5-fluoropentyl)-1H-indol-3-yl)(2-iodophenyl) methanone(AM-694) had strong biological activity.It had been synthesized from indole.In order to make sure the Friedel Crafts acylation catalysted by AlCl3 happened in 3-position of the indole,the benzenesulfonyl chloride was used to protect 1-position of the indole.In this way,it could avoid the high anhydrous and anaerobic requirements when protected by RMgX reagent.Then,further deprotection,N-alkylation,ester hydrolysis,in 1-position of the indole methylsulfonyl esterification were carried out.Finally,compound AM-694 was obtained through tetrabutylammonium fluoride.The content was analyzed by high performance liquid chromatography(HPLC) characterized by nuclear magnetic(NMR) and Mass Spectrometry(MS).The total yield reached 41.8%.Compared with the previous route,the method had advantages of simple,low cost and high yield.