N-bromobutanimide → 7-Bromo-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 (Example 110-F) (1.06 g, 3.53 mmol) in DMF (35.3 mL) at 0° C. was added NBS (0.628 g, 3.53 mmol), and the mixture was stirred at 0° C. After 5 minutes the reaction was quenched with sat. aq. NaHCO3, then with sat. aq. sodium thiosulfate, extracted with EtOAc (2×), dried over MgSO4, filtered and concentrated. The resulting residue was purified by flash chromatography (0-80% EtOAc in heptanes) to provide the title compound, which was used in the next reaction without any further purification. MS (ESI+) m/z 379.0, 380.9 (M+H).

Provenance & Evidence