TY - JOUR
T1 - Synthesis of 6-bromo-2-arylindoles using 2-iodobenzoic acid as precursor
AU - Valois-Escamilla, Ismael
AU - Alvarez-Hernandez, Alejandro
AU - Rangel-Ramos, Luis Felipe
AU - Suárez-Castillo, Oscar Rodolfo
AU - Ayala-Mata, Francisco
AU - Zepeda-Vallejo, Gerardo
N1 - Funding Information:
The authors are grateful for financial support of this work from CONACYT (Grant CB-2006-61247 ) and predoctoral fellowships for I.V. and L.F.R.
PY - 2011/7/20
Y1 - 2011/7/20
N2 - 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.
AB - 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.
KW - 2-Iodobenzoic acid
KW - 6-Bromoindole
KW - Chemoselective coupling
KW - Curtius rearrangement
KW - Sonogashira coupling
UR - http://www.scopus.com/inward/record.url?scp=79959277517&partnerID=8YFLogxK
U2 - 10.1016/j.tetlet.2011.05.040
DO - 10.1016/j.tetlet.2011.05.040
M3 - Artículo
SN - 0040-4039
VL - 52
SP - 3726
EP - 3728
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 29
ER -