N-bromobutanimide → 3-bromo-7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indole

Participants

Reaction Conditions

Reaction Steps

To a solution of 7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indole (D58) (300 mg) in THF (10 mL) was added NBS (160 mg). The reaction mixture was stirred at 20° C. for 16 h. The reaction mixture was concentrated and the residue was purified by column chromatography (15% ethyl acetate in hexane) to afford 3-bromo-7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indole (D59) (330 mg). δH (DMSO-d6, 400 MHz): 1.36 (6H, d), 3.70 (3H, s), 4.88 (1H, m), 7.32 (1H, dd), 7.45 (1H, d), 7.56 (1H, dd), 7.68 (2H, m), 8.12 (1H, dd), 8.20 (1H, d). MS (ES): C20H17BrClN3O2 requires 445; found 446.0 (M+H+).

Provenance & Evidence