4,7-Dichloro-3-iodoquinoline → HCID 89690238, compound

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Reaction Steps

Alternatively, compound 1 can be synthesized according to Scheme 2 by performing the Suzuki coupling directly on the 4-chloro 3-iodo quinoline (C) using dichloro [1,1′ bis(diphenylphosphino)ferrocene)]palladium (II) [PdCl2(dppf)] (Hayashi, T. J. Am. Chem. Soc. 1984, 106, 158-163, incorporated by reference herein) as a catalyst to give 4,7-dichloro-3-(4-(trifluoromethoxy)phenyl)quinoline (P) in 79% yield a white solid after flash chromatography. Finally, the desired product compound 1 is obtained using the same procedure as described in Scheme 2 in approximately 90% yield. In some embodiments, this new and more efficient method (Scheme 2) may give an overall yield of approximately 42%.

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