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Communication | Special issue | Vol 79, No. 1, 2009, pp.427-432
Published online, 11th December, 2008
DOI: 10.3987/COM-08-S(D)70
Synthetic Studies on the Fluorinated Analogs for the Putative Oxindole-Type Metabolites of 5-Halotryptamines

Tomoya Fujiwara, Takayuki Seki, Masaru Miura, and Yoshio Takeuchi*

*Graduate School of Pharmaceutical Sciences, Toyama University, 2630 Sugitani, Toyama, Toyama 930-0194, Japan

Abstract

The suitably protected precursors for direct fluorination, Nb-Boc di-protected 5-fluorotryptamine (13), Nb-acetyl-Nb-Boc protected 5-halotryptamines (15ac), were treated with SelectfluorTM in MeCN/water in the presence of NaHCO3 to give the corresponding 3-fluorooxindoles 14 and 16ac in good yields. Removal of the protecting groups of 14 and 16ac produced (3,5-difluorooxindol-3-yl)ethylamine (8) and N-acetyl-(3-fluoro-5-halooxindol-3-yl)ethylamines (9ac) in excellent yields, respectively. These compounds are potentially non-epimerizable analogs for the putative metabolites of 5-fluorotryptamine (6) and Nb-acetyl-5-halotryptamines (7ac).