Journal of Organic Chemistry p. 5106 - 5110 (1986)
Update date:2022-08-05
Topics:
Moyer, Mikel P.
Shiurba, John F.
Rapoport, Henry
The 4-, 5-, 6-, and 7-bromoindoles, conveniently synthesized by the Batcho-Leimgruber process, serve as efficient precursors to regiochemically pure lithiated indoles.Metal-halogen exchange was most effective if potassium hydride was used first to remove the acidic indole NH, and tert-butyllithium was used then to effect metal-halogen exchange.The resulting indolyl organometallic reagents react with a variety of electrophiles to give regioisomerically pure acylated indoles.
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