Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 70, Issue 25, Pages 10342-10347Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo0514927
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An efficient five-step synthesis of 1,6-naphthyridone 3b, a p38 mitogen-activated protein (MAP) kinase inhibitor intermediate, in 32% overall yield starting from acetonedicarboxylate (ADC) is described. The synthesis began with a selective monoamidation of ADC dimethyl ester enolate 9. A novel concomitant enamine formation and an imide cyclization afforded the nitrogen differentially protected enamide imide 12. Treatment of 12 with (KOBu)-Bu-t and 3-ethoxyacrylate produced lactam 15 quantitatively, which was converted to tetrachloronaphthyridone 19 via a one-pot p-methoxybenzyl (PMB) deprotection and bischlorination. A highly regioselective Pd(OAc)(2)/IMes-catalyzed Suzuki coupling completed the synthesis.
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