CRF ligands via Suzuki and Negishi couplings of 3-pyridyl boronic acids or halides with 2-benzyloxy-4-chloro-3-nitropyridine.
A series of imidazo[4,5-b]pyridines with a 7-(3-pyridyl) substituent is described as high affinity CRF receptor ligands. Individual analogues were synthesized from key intermediates obtained via palladium-catalyzed coupling of 3-pyridyl zinc or boronic acid organometallic intermediates with 2-benzyloxy-4-chloro-3-nitropyridine 12.
Arvanitis
Argyrios G
AG
Discovery Chemistry-Wilmington, Bristol-Myers Squibb Company, Experimental Station, Wilmington, DE 19880, USA. argyrios.arvanitis@bms.com
Arnold
Charles R
CR
Fitzgerald
Lawrence W
LW
Frietze
William E
WE
Olson
Richard E
RE
Gilligan
Paul J
PJ
Robertson
David W
DW
D000818:Animals; D001897:Boronic Acids / Q000737:chemistry; D002384:Catalysis; D002540:Cerebral Cortex / Q000187:drug effects / Q000378:metabolism; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D007093:Imidazoles / Q000138:chemical synthesis* / Q000494:pharmacology*; D066298:In Vitro Techniques; D007202:Indicators and Reagents; D008024:Ligands; D010165:Palladium; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D051381:Rats; D018019:Receptors, Corticotropin-Releasing Hormone / Q000187:drug effects*
C475623:2-benzyloxy-4-chloro-3-nitropyridine; D001897:Boronic Acids; D007093:Imidazoles; D007202:Indicators and Reagents; D008024:Ligands; D011725:Pyridines; D018019:Receptors, Corticotropin-Releasing Hormone; D010165:Palladium