An Efficient Synthesis of the Indole Acetic Acid Metabolite of MK-0462
- 1 May 1996
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 26 (10) , 1977-1984
- https://doi.org/10.1080/00397919608003552
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-HT1D receptor agonist MK-0462.Keywords
This publication has 7 references indexed in Scilit:
- Synthesis and Serotonergic Activity of N,N-Dimethyl-2-[5-(1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethylamine and Analogs: Potent Agonists for 5-HT1D ReceptorsJournal of Medicinal Chemistry, 1995
- Synthesis of the 5-HT1D receptor agonist MK-0462 via a Pd-catalyzed coupling reactionTetrahedron Letters, 1994
- Improved Fischer Indole Reaction for the Preparation of N,N-Dimethyltryptamines: Synthesis of L-695,894, a Potent 5-HT1D Receptor AgonistThe Journal of Organic Chemistry, 1994
- A convenient method for the synthesis of indole-3-acetic acidsTetrahedron Letters, 1994
- Tandem Michael addition–[3,3]sigmatropic rearrangement processes. Part 2. Construction of cyclopropa[3,4]pyrrolo[3,2-e]indol-4-one (CPI) unit of antitumour antibiotic CC-1065Journal of the Chemical Society, Perkin Transactions 1, 1992
- Synthesis of indoles via palladium-catalyzed heteroannulation of internal alkynesJournal of the American Chemical Society, 1991
- The Cyanomethylation of IndoleThe Journal of Organic Chemistry, 1963