Synthesis of disubstituted imidazo[4,5-b]pyridin-2-ones.
Regioselective palladium-catalyzed amination of 2-chloro-3-iodopyridine followed by a subsequent palladium-catalyzed amination leads to 2,3-diaminopyridines. Treatment with triphosgene affords highly functionalized unsymmetrical imidazo[4,5-b]pyridin-2-ones in just three synthetic steps. A two-step synthesis of pseudosymmetrically disubstituted imidazo[4,5-b]pyridin-2-ones, 1,4-disubstituted pyrido[2,3-b]pyrazinediones, and 1,3-disubstituted thiadiazolo[3,4-b]pyridin-2-ones is also described.
Kuethe
Jeffrey T
JT
Department of Process Research, Merck & Co., Inc., P.O. Box 2000, Rahway, New Jersey 07065, USA. jeffrey_kuethe@merck.com
Wong
Audrey
A
Davies
Ian W
IW
D002625:Chemistry, Organic / Q000379:methods*; D007093:Imidazoles / Q000138:chemical synthesis*; D015394:Molecular Structure; D011725:Pyridines / Q000138:chemical synthesis; D011728:Pyridones / Q000138:chemical synthesis*
D007093:Imidazoles; D011725:Pyridines; D011728:Pyridones