title: Regioselective C2-arylation of imidazo[4,5-b]pyridines.
abstract: We show that N3-MEM-protected imidazo[4,5-b]pyridines undergo efficient C2-functionalisation via direct C-H arylation. Twenty-two substituted imidazo[4,5-b]pyridines are prepared and iterative, selective elaboration of functionalised imidazo[4,5-b]pyridines gives 2,7- and 2,6-disubstituted derivatives in good yields from common intermediates. Mechanistic observations are consistent with a concerted-metallation-deprotonation mechanism facilitated by coordination of copper(I)iodide to the imidazo[4,5-b]pyridine.
authors: Cancer Research UK Cancer Therapeutics Unit, Division of Cancer Therapeutics, The Institute of Cancer Research, Haddow Laboratories, Sutton, Surrey SM2 5NG, UK.
authors: Jonathan
authors: J
authors: Macdonald
authors: Victoria
authors: V
authors: Oldfield
authors: Vassilios
authors: V
authors: Bavetsias
authors: Julian
authors: J
authors: Blagg
mesh_terms: D003300:Copper / Q000737:chemistry; D007093:Imidazoles / Q000737:chemistry*; D007454:Iodides / Q000737:chemistry; D015394:Molecular Structure; D011725:Pyridines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D007093:Imidazoles; D007454:Iodides; D011725:Pyridines; D003300:Copper; C073870:cuprous iodide