Benzene → Methyl 4-fluoro-1H-indole-7-carboxylate

Reaktionsgleichung

[F:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]([OH:13])=[O:12])=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[CH:14]1C=CC=CC=1.C[Si](C=[N+]=[N-])(C)C>CO>[F:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]([O:13][CH3:14])=[O:12])=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2

Komponenten

Versuchsvorschrift

To a suspension of 4-fluoro-7-carboxyindole in a mixture of MeOH (18 ml)/PhH (62 ml) was added (trimethylsilyl)diazomethane (8.8 ml, 17.6 mmol, 2 M in hexane). The resulting mixture was stirred at room temperature for 30 min., quenched with excess acetic acid and evaporated in vacuo. The crude oily material was purified by flash chromatography using a gradient elution (Hexane to 10% EtOAc/Hexane) to afford methyl (4-fluoro)indole-7-carboxylate as a white solid (1.04 g, 83% two steps)