Chlorosuccinimide → 7-Chloro-5-methyl-1-tosyl-1H-indol-4-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-methyl-1-tosyl-1H-indol-4-amine (0.52 g, 1.731 mmol) in acetonitrile (17.31 mL) was added NCS (0.231 g, 1.731 mmol), and the mixture was stirred at 50° C. After 2 hours the reaction was cooled to room temperature, quenched with sat. aq. NaHCO3, and with sat. sodium thiosulfate. The layers were separated and the aqueous layer extracted with EtOAc (twice), dried over MgSO4, filtered and concentrated. The resulting residue was purified by flash chromatography (0-80% EtOAc in heptanes) to provide the title compound. MS (ESI+) m/z 335.0 (M+H).

Provenance & Evidence