A Practical and Robust Multistep Continuous Process
for Manufacturing 5‑Bromo‑N‑(tert-butyl)pyridine-3-sulfonamide
Posted on 2019-09-09 - 15:04
A multistep continuous
flow process involving (1) magnesium–halogen
exchange, (2) sulfonylation with sulfuryl chloride, and (3) reaction
with tert-butylamine was developed for the synthesis
of an arylsulfonamide pharmaceutical intermediate in the synthesis
of BMS-919373. The process was successfully implemented, including
a robust control strategy to manage the levels of several process
impurities, to produce 76 kg of 5-bromo-N-(tert-butyl)pyridine-3-sulfonamide (2). As the
instability of the reactive intermediates and existence of strong
exotherms made a batch process unsuitable for production beyond a
1 kg scale, the alternative continuous process led to a practical
and robust manufacturing route to the active pharmaceutical ingredient.
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Yu, Miao; Strotman, Neil A.; Savage, Scott A.; Leung, Simon; Ramirez, Antonio (2019). A Practical and Robust Multistep Continuous Process
for Manufacturing 5‑Bromo‑N‑(tert-butyl)pyridine-3-sulfonamide. ACS Publications. Collection. https://doi.org/10.1021/acs.oprd.9b00254