A concise synthesis of a novel antiangiogenic tyrosine kinase inhibitor.
An efficient synthesis of the potent KDR inhibitor 3-[5-[[4-(methylsulfonyl)-1-piperazinyl]methyl]-1H-indole-2-yl]quinolin-2(1H)-one (1) is described. The process features a noncryogenic indole boronation and a dicyclohexylamine-mediated Suzuki coupling.
Payack
Joseph F
JF
Department of Process Research, Merck & Co. Inc., P.O. Box 2000, Rahway, New Jersey 07065-0900, USA. joseph_payack@merck.com
Vazquez
Enrique
E
Matty
Louis
L
Kress
Michael H
MH
McNamara
James
J
D020533:Angiogenesis Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D007202:Indicators and Reagents; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D010879:Piperazines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011505:Protein-Tyrosine Kinases / Q000037:antagonists & inhibitors*
C496486:3-(5-((4-(methylsulfonyl)-1-piperazinyl)methyl)-1H-indole-2-yl)quinolin-2(1H)-one; D020533:Angiogenesis Inhibitors; D007202:Indicators and Reagents; D007211:Indoles; D010879:Piperazines; D011505:Protein-Tyrosine Kinases