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An efficient and regioselective synthesis of 4- and 7-alkoxyindoles has been develo
ped from commerciallyavailable starting materials such as 3-halo
phenols and 3-chloroanisole. Directed ortho-metalation followedby two
palladium-catalyzed
processes, a Sonogashira cou
pling and a tandem amination/cyclization reaction,allows the synthesis of regiochemically
pure 4- and 7-substituted indoles. This strategy has beensuccessfully a
pplied to the
pre
paration of 2-[3-(2-amino-2-oxoacetyl)-1-benzyl-2-ethyl-1
H-indol-4-yloxy]acetic acid (LY315920), a known inhibitor of
phos
pholi
pase A
2.