Application of an almost traceless linker in the synthesis of 2-alkylthiobenzimidazole combinatorial libraries.
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.
Slade
R M
RM
SIDDCO, Tucson, AZ 85747, USA. sladeboy@earthlink.net
Phillips
M A
MA
Berger
J G
JG
D000473:Alkanes / Q000737:chemistry; D001562:Benzimidazoles / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D009578:Nitrobenzenes / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000737:chemistry
C413652:4-fluoro-3-nitrobenzyl bromide; D000473:Alkanes; D001562:Benzimidazoles; D009578:Nitrobenzenes; D009943:Organophosphorus Compounds; D013438:Sulfhydryl Compounds; C061896:triphenylphosphine