A two-step synthesis of aminopropylpiperidines via aminopropargylpyridines, suitable for the synthesis of a new class of 5-HT4 ligands |
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Authors: | Olivier Russo Jean-Daniel Brion Isabelle Berque-Bestel |
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Affiliation: | a Laboratoire de Reconnaissance Moléculaire et Synthèse, BioCIS-CNRS (UMR 8076), Université Paris-Sud, Faculté de Pharmacie, rue J.B. Clément 92296 Châtenay-Malabry Cedex, France b Laboratoire de Chimie Thérapeutique, BioCIS-CNRS (UMR 8076), Université Paris-Sud, Faculté de Pharmacie, rue J.B. Clément 92296 Châtenay-Malabry Cedex, France |
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Abstract: | A rapid and flexible synthetic approach to {[bis(tert-butoxycarbonyl)amino]propyl}piperidines 5 and related compounds is described. The key step is a three-component coupling process of 2-, 3- or 4-bromopyridine, propargyl bromide and potassium di-tert-butyliminodicarbonate under palladium-copper catalysis leading to 2-, 3- or 4-{[bis(tert-butoxycarbonyl)amino]-propargyl}pyridines 4 followed by a catalytic reduction step. |
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Keywords: | Sonogashira Palladium Aminopropylpiperidine Aminopropargylpyridine 5-HT4 ligands |
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