Synthesis of 2-(Chlorodifluoromethyl)indoles for Nucleophilic Halogen Exchange with [18F]Fluoride

Bock L, Schultheiss SK, Maschauer S, Lasch R, Gradl S, Prante O, Zard SZ, Heinrich M (2021)

Publication Type: Journal article

Publication year: 2021

Journal

European Journal of Organic Chemistry Wiley

Book Volume: 2021

Pages Range: 6258-6262

Journal Issue: 46

DOI: 10.1002/ejoc.202100937

Abstract

The synthesis of 2-[¹⁸F]trifluoromethylated indoles from the corresponding chlorodifluoromethyl precursors was found to proceed under milder conditions when compared to known metal-free nucleophilic exchange reactions with [¹⁸F]fluoride on chlorodifluoro-methyl arenes. A key element in the reaction course is – most likely – a favorable elimination-addition mechanism on the 2-methyl position of the indole. Given the increasing interest in ¹⁸F-labelled compounds, this single step labeling methodology nicely complements the so far existing routes to 2-[¹⁸F]trifluoromethylated indoles.

Authors with CRIS profile

Leonard Bock Professur für Pharmazeutische Chemie Simone Maschauer Department of Nuclear Medicine Roman Lasch Professur für Pharmazeutische Chemie Susanne Gradl Professur für Pharmazeutische Chemie Olaf Prante Professur für Molekulare Bildgebung und Radiochemie Markus Heinrich Professur für Pharmazeutische Chemie

Involved external institutions

École Polytechnique - Université Paris-Saclay

France (FR)

How to cite

APA:

Bock, L., Schultheiss, S.K., Maschauer, S., Lasch, R., Gradl, S., Prante, O.,... Heinrich, M. (2021). Synthesis of 2-(Chlorodifluoromethyl)indoles for Nucleophilic Halogen Exchange with [18F]Fluoride. European Journal of Organic Chemistry, 2021(46), 6258-6262. https://dx.doi.org/10.1002/ejoc.202100937

MLA:

Bock, Leonard, et al. "Synthesis of 2-(Chlorodifluoromethyl)indoles for Nucleophilic Halogen Exchange with [18F]Fluoride." European Journal of Organic Chemistry 2021.46 (2021): 6258-6262.

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