Abstract Lithium diisopropylamide reacts with 2-fluoropyridine at low temperature: regioselectivity is excellent and metallation occurs without side reactions such as nucleophilic attack. 2-Fluoro-3-lithiopyridine is formed and with aldehydes it gives the corresponding fluorinated alcohols which are then selectively oxidized. Halogen substitution using amines leads to various 3-oxoalkyl-or 3-aroyl-2-aminopyridines.