Oxidation of methyl heteroaryls with molecular oxygen:: A facile synthesis of 2-[N-(tert-butoxycarbonyl)amino]-4-pyridinecarbaldehyde

Oxidation of nitrogen-based methyl heteroaryls with molecular oxygen resulted in the formation of the corresponding benzyl alcohols. While experimentally easy and amenable to large-scale preparations, this approach has limitations with respect to the particular nature of heterocyclic substrates. Using this methodology, the title compound, 2-[N-(tert-butoxycarbonyl)amino]-4-pyridinecarbaldehyde, considered to be a versatile pharmaceutical intermediate, was prepared on a multigram scale.