105205-51-4Relevant articles and documents
Metal-Halogen Exchange of Bromoindoles. A Route to Substituted Indoles
Moyer, Mikel P.,Shiurba, John F.,Rapoport, Henry
, p. 5106 - 5110 (2007/10/02)
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.