Visual monitoring of solid-phase extraction using chromogenic fluorous synthesis supports.
Reductive aminations and further transformations of an azo dye and fluorous tagged aldehyde are described. The intensely colored 2,4-dialkoxybenzyl protected amines undergo Fmoc-based peptide coupling, Suzuki reactions, and sulfonamide formation with product isolation facilitated by visual monitoring of fluorous solid phase extraction. Target compounds are released from the supports in high yields and purities by treatment with trifluoroacetic acid (TFA).
Discovery, Millennium Pharmaceuticals Inc., Cambridge Massachusetts 02139, United States. blackburn@mpi.com
Christopher
C
Blackburn
D001391:Azo Compounds / Q000737:chemistry; D002863:Chromogenic Compounds / Q000737:chemistry*; D005461:Fluorine / Q000737:chemistry*; D015394:Molecular Structure; D052616:Solid Phase Extraction; D013441:Sulfinic Acids / Q000737:chemistry
D001391:Azo Compounds; D002863:Chromogenic Compounds; D013441:Sulfinic Acids; D005461:Fluorine; C044255:sulfonyl chloride