Retrosynthesis of Furan-Containing Pharmaceutical Precursors
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Malek, Marc
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2018-04-20
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Retrosynthesis of Furan-Containing Pharmaceutical Precursors
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Abstract
Herein we report on the retrosynthetic production of 3-iodo-2-(2-methoxyphenyl)-benzofuran in 4 synthetic steps. Benzofuran compounds are found in anti-anxiolytic medications, such as vilazodone, which interact with the brain to counteract symptoms of anxiety and depression. The target molecule was selected as a pharmaceutical precursor, featuring a benzofuran derivative coupled to a synthetic handle that will allow for further functionalization. This planned synthesis utilized starting materials of 2-iodoanisole and ethynyltrimethylsilane under Sonogashira conditions, a deprotection reaction, and a cyclization reaction. The highest synthetic step achieved was the production of bis(2-methoxyphenyl)acetylene in 99% yield. Cyclization of this compound is currently underway.