1315267-73-2Relevant articles and documents
Synthesis of 6-bromo-2-arylindoles using 2-iodobenzoic acid as precursor
Valois-Escamilla, Ismael,Alvarez-Hernandez, Alejandro,Rangel-Ramos, Luis Felipe,Suárez-Castillo, Oscar Rodolfo,Ayala-Mata, Francisco,Zepeda-Vallejo, Gerardo
, p. 3726 - 3728 (2011/08/06)
The synthesis of 6-bromo-2-arylindoles starting from readily available 2-iodobenzoic acid is presented. Regioselective bromination of the latter was followed by Curtius rearrangement and trapping of the isocyanate with benzyl alcohol led to the benzyl carbamate of 2-iodo-5-bromoaniline. Chemoselective Sonogashira coupling of this compound with arylacetylenes followed by TBAF induced 5-endo-dig cyclization gave the desired bromo indoles. The method allows selective introduction of a bromine atom at the indole C-6 position.