Journal
ORGANIC PROCESS RESEARCH & DEVELOPMENT
Volume 19, Issue 7, Pages 865-871Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.oprd.5b00131
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A large-scale process for the synthesis of SYK inhibitor 1 has been developed and used to deliver multi-kilogram yields of this active pharmaceutical ingredient. Integral to the scalable process is a combined chiral auxiliary and chiral catalyst mediated diastereoselective fluorination. Safe processes for BH3 center dot DMS-mediated reduction of ester and amide functions and azide introduction, and a robust Suzuki-Miyaura coupling of a pyrazyl boronate with chloronapthyridine, are described.
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