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Org Lett. 2006 Aug 17;8(17):3805-8.

Facile one-pot synthesis of N-difluoromethyl-2-pyridone derivatives.

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  • 1Tsukuba Research Institute, Banyu Pharmaceutical Company, Ltd., Okubo 3, Tsukuba 300-2611, Japan.


[reaction: see text] A novel one-pot synthesis of N-difluoromethyl-2-pyridones is described. N-(Pyridin-2-yl)acetamide derivatives were excellent precursors for the preparation of N-difluoromethyl-2-pyridone derivatives. Difluoromethylation of 2-acetaminopyridine derivatives was achieved with sodium chlorodifluoroacetate as a difluorocarbene source in the presence of a catalytic amount of 18-crown-6. Subsequent in situ hydrolysis of resultant 1,2-dihydro-2-acetimino-1-difluoromethylpyridines proceeded under mild acidic conditions to afford the corresponding N-difluoromethyl-2-pyridones in moderate to good yields.

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