Title of article
Synthesis of 6-bromo-2-arylindoles using 2-iodobenzoic acid as precursor
Author/Authors
Valois-Escamilla، نويسنده , , Ismael and Alvarez-Hernandez، نويسنده , , Alejandro and Rangel-Ramos، نويسنده , , Luis Felipe and Suلrez-Castillo، نويسنده , , Oscar Rodolfo and Ayala-Mata، نويسنده , , Francisco and Zepeda-Vallejo، نويسنده , , Gerardo، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2011
Pages
3
From page
3726
To page
3728
Abstract
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.
Keywords
Curtius rearrangement , Sonogashira coupling , 6-Bromoindole , Chemoselective coupling , 2-iodobenzoic acid
Journal title
Tetrahedron Letters
Serial Year
2011
Journal title
Tetrahedron Letters
Record number
1878767
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