Convergent synthesis of the quinolone substructure of BILN 2061 via carbonylative Sonogashira coupling/cyclization.
A convergent synthesis of quinolone 2 (key substructure of the protease inhibitor BILN 2061) was developed via palladium-catalyzed carbonylation of 2-iodo-5-methoxyaniline (4) with thiazolylacetylene 5.
Haddad
Nizar
N
Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc., 900 Ridgebury Rd., P.O. Box 368, Ridgefield, Connecticut 06877-0368, USA. nhaddad@rdg.boehringer-ingelheim.com
Tan
Jonathan
J
Farina
Vittorio
V
D000480:Alkynes / Q000737:chemistry*; D002219:Carbamates / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D006847:Hydrocarbons, Iodinated / Q000737:chemistry; D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D015363:Quinolones / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry
D000480:Alkynes; C479555:BILN 2061; D002219:Carbamates; D006847:Hydrocarbons, Iodinated; D047028:Macrocyclic Compounds; D011804:Quinolines; D015363:Quinolones; D013844:Thiazoles; D010165:Palladium