Retrosynthesis of Furan-Containing Pharmaceutical Precursors

No Thumbnail Available
Authors
Malek, Marc
Advisor
Editor
Date of Issue
2018-04-20
Subject Keywords
Publisher
Citation
Series/Report No.
item.page.identifier
Title
Retrosynthesis of Furan-Containing Pharmaceutical Precursors
Other Titles
Type
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.
Sponsors
Degree Awarded
Semester
Department