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Continuous flow synthesis of Celecoxib from 2-bromo-3,3,3-trifluoropropene

Continuous flow synthesis of Celecoxib from 2-bromo-3,3,3-trifluoropropene We describe the total flow synthesis of the widely prescribed anti-inflammatory COX-2 inhibitor Celecoxib from 2-bromo-3,3,3-trifluoropropene, as a convenient and available trifluoromethyl building block, to generate trifluoropropynyl lithium and to trap it immediately with an aldehyde. Oxidation of the obtained alcohol into ketone followed by condensation with 4-sulfamidophenylhydrazine afforded the targeted drug with full regioselectivity. It is noteworthy that the quality of these flow reactions (50% overall yield within 1 h cumulated residence time over 3 steps) directly furnished the target API and intermediates with excellent purity.Graphical abstract[graphic not available: see fulltext] http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Journal of Flow Chemistry Springer Journals

Continuous flow synthesis of Celecoxib from 2-bromo-3,3,3-trifluoropropene

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Publisher
Springer Journals
Copyright
Copyright © Akadémiai Kiadó 2021
ISSN
2062-249X
eISSN
2063-0212
DOI
10.1007/s41981-021-00205-x
Publisher site
See Article on Publisher Site

Abstract

We describe the total flow synthesis of the widely prescribed anti-inflammatory COX-2 inhibitor Celecoxib from 2-bromo-3,3,3-trifluoropropene, as a convenient and available trifluoromethyl building block, to generate trifluoropropynyl lithium and to trap it immediately with an aldehyde. Oxidation of the obtained alcohol into ketone followed by condensation with 4-sulfamidophenylhydrazine afforded the targeted drug with full regioselectivity. It is noteworthy that the quality of these flow reactions (50% overall yield within 1 h cumulated residence time over 3 steps) directly furnished the target API and intermediates with excellent purity.Graphical abstract[graphic not available: see fulltext]

Journal

Journal of Flow ChemistrySpringer Journals

Published: Jun 1, 2022

Keywords: Organofluorine chemistry; Active pharmaceutical ingredients; Organolithium chemistry; Oxidation; NSAID

References