Abstract
An efficient and regioselective synthesis of 4- and 7-alkoxyindoles has been developed from commercially available starting materials such as 3-halophenols and 3-chloroanisole. Directed ortho-metalation followed by two palladium-catalyzed processes, a Sonogashira coupling and a tandem amination/cyclization reaction, allows the synthesis of regiochemically pure 4- and 7-substituted indoles. This strategy has been successfully applied to the preparation of 2-[3-(2-amino-2-oxoacetyl)-1-benzyl-2-ethyl-1H-indol-4-yloxy]acetic acid (LY315920), a known inhibitor of phospholipase A2.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkanes / chemical synthesis*
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Alkylation
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Anisoles / chemistry*
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Enzyme Inhibitors / chemical synthesis*
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Enzyme Inhibitors / chemistry
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Enzyme Inhibitors / pharmacology
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Ethers / chemistry
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Indoles / chemical synthesis*
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Indoles / chemistry
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Molecular Structure
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Oxygen / chemistry
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Phenols / chemistry*
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Phospholipases A / antagonists & inhibitors*
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Phospholipases A / metabolism
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Phospholipases A2
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Stereoisomerism
Substances
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3-chloroanisole
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Alkanes
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Anisoles
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Enzyme Inhibitors
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Ethers
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Indoles
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Phenols
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indole
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Phospholipases A
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Phospholipases A2
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Oxygen