ORGN 558 |
The Fu Suzuki reaction, a room-temperature variant of the classic Suzuki coupling reaction using P(t-Bu)3 and a palladium source, was employed for the key carbon-carbon bond forming step in the kilogram-scale preparation of a clinical candidate. Thus the thermally-sensitive o-cyanophenylboronic acid 1 was coupled with aryl bromide 2 in high yield and purity at room temperature to afford late-stage pharmaceutical intermediate 3 on multigram and kilogram scale. Reaction enablement, optimization, general and substrate-specific scope and limitations will be detailed, and other findings encountered while implementing this methodology on kilogram scale will be presented.
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Heterocycles, Aromatics, Metal-Mediated Reactions and Syntheses, Materials, Devices, and Switches
8:00 PM-10:00 PM, Wednesday, 29 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster
Division of Organic Chemistry |