A Convergent Continuous Multistep Process for the Preparation of C4-Oxime-Substituted Thiazoles

    • Edouard Godineau *†
    • Claudio Battilocchio †‡
    • Matthias Lehmann
    • Steven V. Ley
    • Ricardo Labes
    • Letitia Birnoschi
    • Srinivas Subramanian §
    • C.S Prasanna §
    • Amol Gorde §
    • Mahesh Kalbagh §
    • Vivek Khade §
    • Anton Scherrer
    • Anthony C. O’Sullivan
    • Syngenta Crop Protection, Process Research, Schaffhauserstrasse 101, CH-4332, Switzerland
    • Innovative Technology Centre, Department of Chemistry, University of Cambridge, Lensfield Road, CB2 1EW, UK
    • § Syngenta Research and Technology Centre, Santa Monica Works, Corlim, Goa India, 403110

    We report a strategy designed for the rapid and convergent assembly of C4-oxime substituted thiazoles. Our approach relied on 3-bromo-2-oxopropanal O-methyl oxime 7 as a key building block. A three-step sequence to 7 was designed, which, for safety concerns, could only be operated in batch mode on limited scales (≪100 g). We describe herein how we addressed such a limitation, by designing a multistep continuous synthesis of this intermediate and further demonstrate the advantages of flow reactor configuration upon scaling up.

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