A series of 3-(2-haloalkenyl)-2-pyridyl-halides undergo consecutive palladium-catalysed inter-and intramolecular amination reactions to deliver a series of 1-functionalised 7- azaindoles. Anilines and amines can be readily employed as the N-nucleophile and incorporation of both electron-donating and electron withdrawing substituents on the pyridine core is possible.