A concise synthesis of all four possible benzo[4,5]furopyridines via palladium-mediated reactions.
[reaction: see text] By taking advantage of the alpha- and gamma-activation of chloropyridines as well as palladium-mediated reactions, all four possible benzo[4,5]furopyridine tricyclic heterocycles, benzo[4,5]furo[2,3-b]pyridine, benzo[4,5]furo[2,3-c]pyridine, benzo[4,5]furo[3,2-c]pyridine, and benzo[4,5]furo[3,2-b]pyridine, are efficiently synthesized from 2-chloro-3-iodopyridine, 3-chloro-4-stannylpyridine, 4-chloro-3-iodopyridine, and 2-chloro-3-hydroxypyridine, respectively.
Yue
Wen Song
WS
Department of Chemistry, Pfizer Global Research and Development, 2800 Plymouth Road, Ann Arbor, Michigan 48105, USA.
Li
Jie Jack
JJ
D001572:Benzofurans / Q000138:chemical synthesis*; D002384:Catalysis; D002713:Chlorine; D010165:Palladium / Q000737:chemistry; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry
D001572:Benzofurans; D011725:Pyridines; D002713:Chlorine; D010165:Palladium