High-throughput combinatorial synthesis of substituted benzimidazolones

An efficient liquid-phase synthesis of substituted benzimidazolones 7 is described. Resin bound o-fluoronitrobenzene 1 is reacted with various primary amines to afford o-nitroaniline derivatives 2. Subsequent reduction of the aromatic nitro group followed by cyclization gives a PEG bound benzimidazole-2-one 4. N-Alkylation of this resin bound scaffold 4 with several electrophiles gives the resulting library in excellent yield and purity after cleavage. (C) 1999 Elsevier Science Ltd. All rights reserved.