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Synthesis of [ 2 H 5 ]baricitinib via [ 2 H 5 ]ethanesulfonyl chloride
Author(s) -
Jansenvan Vuuren Ross D.,
Vohra Rahul
Publication year - 2022
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.3969
Subject(s) - chemistry , yield (engineering) , deuterium , isotope , chloride , combinatorial chemistry , radiochemistry , organic chemistry , thermodynamics , nuclear physics , physics
Baricitinib, typically applied as a treatment for rheumatoid arthritis, has recently attracted the attention of clinicians and researchers as a potential treatment for COVID‐19. Naturally, there has been a need for the preparation of the isotope‐labelled analogue of baricitinib to probe the pharmacokinetics of baricitinib in this new role. As such, we have developed a simple synthetic route to deuterated [ 2 H 5 ]baricitinib, facilitating its formation over four steps and in a 29% overall yield based on starting [ 2 H 5 ]ethanethiol (19% if we start with [ 2 H 5 ]bromoethane instead). A critical component of the overall process involves the synthesis of [ 2 H 5 ]ethanesulfonyl chloride, and we describe in detail the two routes that were explored to optimize this step.