Synthesis of 5-Substituted-1 H-indol-2-yl-1 H-quinolin-2-ones: A Novel Class of KDR Kinase Inhibitors

JT Kuethe, A Wong, C Qu, J Smitrovich…

Index: Kuethe, Jeffrey T.; Wong, Audrey; Qu, Chuanxing; Smitrovich, Jacqueline; Davies, Ian W.; Hughes, David L. Journal of Organic Chemistry, 2005 , vol. 70, # 7 p. 2555 - 2567

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Citation Number: 97

Abstract

A number of approaches for the synthesis of the 1 H-indol-2-yl-1 H-quinolin-2-one ring system found in the potent and selective KDR kinase inhibitor 1 are described. The preparation and reaction of trimethylsilylnitrobenzene 26 with 2-methoxy-3- quinolinecarboxaldehyde 28 afforded alcohol 30, which was the key intermediate for the preparation of the target compounds. Conversion of alcohol 30 to either nitroketone 36 or ...