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

    • Maria Ivanova1
    • Julien Legros1
    • Thomas Poisson1,2
    • Philippe Jubault1
    • 1INSA Rouen, CNRS, UNIROUEN, COBRA, Normandie Univ, 76000 Rouen, France
    • 2Institut Universitaire de France, 1 Rue Descartes, 75231 Paris, France

    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.

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