Industrial Catalytic Processes for Fine and Specialty Chemicals 2016
DOI: 10.1016/b978-0-12-801457-8.00012-4
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Use of Catalysis for API Manufacturing

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“…While significant synthetic efforts were previously undertaken for the structurally similar MK-7246, the presence of a fluorine atom on the indole and a 1,5-disubstituted 1,2,3-triazole side chain in MK-1029 necessitated the investigation of alternative chemistry to address critical bond disconnections. In considering a disconnection strategy for MK-1029, the cornucopia of catalytic methods developed over the last 20 years provided a diverse toolkit that was well-suited for developing an efficient and sustainable synthesis . Herein we present the first Good Manufacturing Practice (GMP) delivery route toward MK-1029, which incorporates five unique catalytic transformations, specifically (1) imine-Heck reaction (palladium), (2) N–H insertion (iridium), (3) asymmetric ketone reduction (ketoreductase), (4) Sonogashira reaction (palladium), and (5) azide–alkyne cycloaddition (ruthenium).…”
mentioning
confidence: 99%
“…While significant synthetic efforts were previously undertaken for the structurally similar MK-7246, the presence of a fluorine atom on the indole and a 1,5-disubstituted 1,2,3-triazole side chain in MK-1029 necessitated the investigation of alternative chemistry to address critical bond disconnections. In considering a disconnection strategy for MK-1029, the cornucopia of catalytic methods developed over the last 20 years provided a diverse toolkit that was well-suited for developing an efficient and sustainable synthesis . Herein we present the first Good Manufacturing Practice (GMP) delivery route toward MK-1029, which incorporates five unique catalytic transformations, specifically (1) imine-Heck reaction (palladium), (2) N–H insertion (iridium), (3) asymmetric ketone reduction (ketoreductase), (4) Sonogashira reaction (palladium), and (5) azide–alkyne cycloaddition (ruthenium).…”
mentioning
confidence: 99%