The Synthesis of (S)-5-Fluoro-1-(2-fluorophenyl)-3-(piperidin-3-ylmethoxy)-1H-indazole, a Norepinephrine/Serotonin Reuptake Inhibitor for the Treatment of Fibromyalgia

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• 作者：Javier Magano ; Michael Waldo ; Derek Greene ; Eric Nord
• 刊名：Organic Process Research & Development
• 出版年：2008
• 出版时间：September 19, 2008
• 年：2008
• 卷：12
• 期：5
• 页码：877-883
• 全文大小：187K
• 年卷期：v.12,no.5(September 19, 2008)
• ISSN：1520-586X

文摘

Compound 1, a norepinephrine/serotonin reuptake inhibitor (NSRI) for the treatment of fibromyalgia, has been synthesized in optically pure form in six linear steps and 48% overall yield with no chromatography. This route features a novel and efficient intramolecular cyclization to generate the indazolone core via a diazotization reaction and the preparation of a stable polymorph of the tartaric acid salt as the desired final form. The original synthetic route has been modified to avoid the use of toxic and expensive reagents, thus enabling the preparation of multigram quantities of API for toxicology studies.