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Synfacts 2011(3): 0244-0244  
DOI: 10.1055/s-0030-1259403
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Indomethacin and Iprindole

Contributor(s): Philip Kocienski
B. A. Haag, Z.-G. Zhang, J.-S. Li, P. Knochel*
Ludwig-Maximilians-Universität München, Germany and Nankai University, Tianjin, P. R. of China
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Publication History

Publication Date:
16 February 2011 (online)

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Significance

A synthesis of indomethacin (anti-inflammatory) illustrates a new organometallic variation of the Fischer indole synthesis that incorporates the nucleophilic addition of an organozinc reagent to an aryldiazonium salt (B + C → D) as the key step. Tautomerization of the azo intermediate D gave the arylhydrazone E, an intermediate in the classical Fischer indole synthesis. A related synthesis of iprindole is also described.