Novel 2,2-Bipyridine Ligand for Palladium-Catalyzed Regioselective Carbonylation
Organic Letters1999Vol. 1(5), pp. 745–747
Citations Over TimeTop 10% of 1999 papers
Abstract
[reaction: see text] A palladium-catalyzed highly regioselective one-step carbonylation of 2,5-dibromo-3-methylpyridine is reported. A range of alkyl esters and amides can be prepared in good yield with better than 95:5 regioselectivity via this method. Key to the high regioselectivity for the formation aromatic amides is the introduction of a novel nonphosphine-based 2,2-bipyridine ligand. This novel reaction was scaled up smoothly in the plant to a 130-kg batch size and facilitated the delivery of bulk material for the clinical trials of Sch 66336, a candidate for oncologic treatments.
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