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Article Dans Une Revue Journal of flow chemistry Année : 2021

Continuous Flow Synthesis of Celecoxib from 2-Bromo-3,3,3-Trifluoropropene

Résumé

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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Dates et versions

hal-03838948 , version 1 (03-11-2022)

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Maria Ivanova, Julien Legros, Thomas Poisson, Philippe Jubault. Continuous Flow Synthesis of Celecoxib from 2-Bromo-3,3,3-Trifluoropropene. Journal of flow chemistry, 2021, 12 (2), pp.147-151. ⟨10.1007/s41981-021-00205-x⟩. ⟨hal-03838948⟩
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