Solid-phase synthesis of substituted benzimidazoles

✍ Scribed by David Tumelty; Matthias K. Schwarz; Kathy Cao; Michael C. Needels

• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 216 KB
• Volume: 40
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(99)01299-x

✦ Synopsis

A solid-phase synthesis of benzimidazoles, substituted on the aromatic ring by a variety of groups or atoms, is described. Intermediate 3, derived from the acylation of a resin-bound secondary amine with Fmoc-glycine, was elaborated via nucleophilic displacement with substituted o-halonitroarenes to give 4. Careful optimization of the subsequent nitro-group reduction and cyclization with aldehydes, followed by acidolysis gave the title compounds 7 in good yields and purities.