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

Organic letters (2006-08-11)
Makoto Ando, Toshihiro Wada, Nagaaki Sato
ABSTRACT

[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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
2,2-Difluoro-2-(fluorosulfonyl)acetic acid, 97%
Sigma-Aldrich
5-Bromo-2(1H)-pyridone, 97%