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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