Application of an almost traceless linker in the synthesis of 2-alkylthiobenzimidazole combinatorial libraries
Rachel M. Slade, Margo A. Phillips, Joel G. Berger
Abstract
Resin-bound triphenylphosphine was coupled to 4-fluoro-3-nitrobenzyl
bromide, and 2-alkylthiobenzimidazoles were synthesized on resin in 4
steps using standard chemistries. Cleavage of the compounds from the resin
was achieved with 10% NaOH in MeOH to leave a methyl group at the
attachment point. A total of 47 amines and 40 electrophiles were
evaluated, defining the scope of the reactions, culminating in the
synthesis of an 80-member test library of high purity as determined by
HPLC.
Keywords
alkylthiobenzimidazole, combinatorial chemistry, phosphonium resin, solid
phase synthesis, traceless linker
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