A Practical Synthesis of 6-[2-(2,5-Dimethoxyphenyl)ethyl]-4-ethylquinazoline and the Art of Removing Palladium from the Products of Pd-Catalyzed Reactions
Organic Process Research & Development2003Vol. 7(5), pp. 733–742
Citations Over TimeTop 10% of 2003 papers
Kurt Königsberger, Guang‐Pei Chen, Raeann Wu, Michael Girgis, Kapa Prasad, Oljan Repič, Thomas J. Blacklock
Abstract
A concise large-scale synthesis of 1, a new antimitotic agent is described. The key step was a one-pot Sonogashira cross-coupling of an aryl halide with a heteroaryl halide through an acetylene using the readily available 2-methyl-3-butyn-2-ol (7). An innovative approach for palladium removal was designed and successfully scaled-up on a multikilogram scale. The product was crystallized from the crude reaction mixture while keeping the residual palladium in the mother liquor by using Pd-scavenging agents such as N-acetylcysteine or thiourea.
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