Solid-phase bromination and Suzuki coupling of 2-carboxyindoles.
As part of an ongoing lead discovery project we have developed a convenient method for the modification and substitution of indole moieties at the 3-position. Selective bromination of three different 2-carboxyindoles was followed by Suzuki cross-coupling with aryl and heteroaryl boronic acids on a Merrifield resin solid-phase. After column chromatography, yields of the 3- substituted indoles ranged from 42-98%.
Tois
J
J
Division of Pharmaceutical Chemistry, Department of Pharmacy, University of Helsinki, P. O. Box 56, FIN-00014 Helsinki, Finland. Jan.Tois@helsinki.fi
Franzén
R
R
Aitio
O
O
Laakso
I
I
Huuskonen
J
J
Taskinen
J
J
D001966:Bromine; D002264:Carboxylic Acids / Q000138:chemical synthesis / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D021241:Spectrometry, Mass, Electrospray Ionization; D013329:Structure-Activity Relationship
D002264:Carboxylic Acids; D007211:Indoles; D001966:Bromine