Title

Retrosynthesis of Furan-Containing Pharmaceutical Precursors

Venue

Campus Center

Major

Chemistry

Field of Study

Chemistry

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.

Start Date

20-4-2018 9:00 AM

End Date

20-4-2018 10:00 AM

Comments

Abstract Only

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Apr 20th, 9:00 AM Apr 20th, 10:00 AM

Retrosynthesis of Furan-Containing Pharmaceutical Precursors

Campus Center

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.