CRF ligands via Suzuki and Negishi couplings of 3-pyridyl boronic acids or halides with 2-benzyloxy-4-chloro-3-nitropyridine

Argyrios G Arvanitis; Charles R Arnold; Lawrence W Fitzgerald; William E Frietze; Richard E Olson; Paul J Gilligan; David W Robertson

doi:10.1016/s0960-894x(02)00835-1

CRF ligands via Suzuki and Negishi couplings of 3-pyridyl boronic acids or halides with 2-benzyloxy-4-chloro-3-nitropyridine

Bioorg Med Chem Lett. 2003 Jan 20;13(2):289-91. doi: 10.1016/s0960-894x(02)00835-1.

Authors

Argyrios G Arvanitis¹, Charles R Arnold, Lawrence W Fitzgerald, William E Frietze, Richard E Olson, Paul J Gilligan, David W Robertson

Affiliation

¹ Discovery Chemistry-Wilmington, Bristol-Myers Squibb Company, Experimental Station, Wilmington, DE 19880, USA. [email protected]

PMID: 12482442
DOI: 10.1016/s0960-894x(02)00835-1

Abstract

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.

MeSH terms

Animals
Boronic Acids / chemistry
Catalysis
Cerebral Cortex / drug effects
Cerebral Cortex / metabolism
Chemical Phenomena
Chemistry, Physical
Imidazoles / chemical synthesis*
Imidazoles / pharmacology*
In Vitro Techniques
Indicators and Reagents
Ligands
Palladium
Pyridines / chemical synthesis*
Pyridines / chemistry
Pyridines / pharmacology*
Rats
Receptors, Corticotropin-Releasing Hormone / drug effects*

Substances

2-benzyloxy-4-chloro-3-nitropyridine
Boronic Acids
Imidazoles
Indicators and Reagents
Ligands
Pyridines
Receptors, Corticotropin-Releasing Hormone
Palladium