Synthesis and reactivity of pyrrolo[3,2-e]indole: Removal of a N-BOM group from an unactivated indole

✍ Scribed by John E. Macor; James T. Forman; Ronald J. Post; Kevin Ryan

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 202 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(97)00198-6

✦ Synopsis

A practical synthesis of pyrrolo [3,2-e]indole (1) is described. Different hydrogenation conditions of the indol-4-ylacetonitrile (3) afforded either l-BOM-pyrrolo[3,2-e]indole (4, 42% from 5nitroindole) or I-hydroxymethylpyrrolo[3,2-e]indole (5, 46% from 5-nitroindole). Removal of the benzyl group was found to be problematic, but could be accomplished in moderate yield. Treatment of the resulting l-hydroxymethylpyrrolo[3,2-e]indole (5) with NaOH in THF afforded I (94% from 5). Limited studies on the chemistry of I are also presented.