An Efficient Synthesis of the Indole Acetic Acid Metabolite of MK-0462

Cheng-yi Chen Department of Process Research, Merck Research Laboratories Division of Merck & Co., Inc., P. O. Box 2000, Rahway, New Jersey, 07065, USA

David R. Lieberman Department of Process Research, Merck Research Laboratories Division of Merck & Co., Inc., P. O. Box 2000, Rahway, New Jersey, 07065, USA

Leslie J. Street Neuroscience Research Centre Merck Sharp & Dohme Research, Laboratories Terlings Park Harlow, Essex, CM20 2QR, U. K.

Alex R. Guiblin Neuroscience Research Centre Merck Sharp & Dohme Research, Laboratories Terlings Park Harlow, Essex, CM20 2QR, U. K.

Robert D. Larsen Department of Process Research, Merck Research Laboratories Division of Merck & Co., Inc., P. O. Box 2000, Rahway, New Jersey, 07065, USA

Thomas R. Verhoeven Department of Process Research, Merck Research Laboratories Division of Merck & Co., Inc., P. O. Box 2000, Rahway, New Jersey, 07065, USA

Abstract

A palladium-catalyzed coupling of iodoaniline 2 with bis-TES propargyl alcohol 3 gives indole-3-methanol 4b in 72% yield. Displacement of the hydroxy group of 4b by sodium cyanide followed by hydrolysis of the cyano group and desilylation provides the indole acetic acid metabolite, L-749,335 (1), of the 5-HT_1D receptor agonist MK-0462.

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An Efficient Synthesis of the Indole Acetic Acid Metabolite of MK-0462

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An Efficient Synthesis of the Indole Acetic Acid Metabolite of MK-0462

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