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    Retrosynthesis of Furan-Containing Pharmaceutical Precursors

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    Author
    Malek, Marc
    Date of Issue
    2018-04-20
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    URI
    https://scholars.carroll.edu/handle/20.500.12647/7105
    Title
    Retrosynthesis of Furan-Containing Pharmaceutical Precursors
    Description
    Abstract Only
    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.
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