Facile substitution of resin-bound indoles via the Mannich reaction

✍ Scribed by Han-Cheng Zhang; Kimberly K. Brumfield; Libuse Jaroskova; Bruce E. Maryanoff

• Book ID: 104259391
• Publisher: Elsevier Science
• Year: 1998
• Tongue: French
• Weight: 230 KB
• Volume: 39
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(98)00844-2

✦ Synopsis

Mannich reaction of resin-bound indoles 1 provided 3-aminomethylindoles 4. Palladiummediated hetemannulation of terminal alkynes with resin-bound o-iodosulfonanilide 7, followed by Mannich reaction, afforded 2-substituted-3-aminomethylindoles 11. Nucleophilic substitution of resinbound 3-dimethylaminomethylindole 12 with KCN or ethyl 2-nitroacetate gave 3-substituted indoles 13 and 14, respectively. High yields and purities were realized for 4, 11, 13, and 14.