Science of Synthesis

Spitzner, D., Science of Synthesis Knowledge Updates, (2016) 1, 171.

Treatment of 5-bromo-2-chloropyridine (‌330‌) with tert-butyllithium or lithium diisopropylamide gives 5-bromo-2-chloro-4-lithio-pyridine, which adds to a second molecule of the substrate. The resulting 1,4-dihydropyridine is oxidized without isolation to give the bipyridine ‌331‌ (‌Scheme 243‌).[‌514‌]

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