N-bromobutanimide → HCID 59451652, compound

Participants

Reaction Steps

NBS (0.670 g, 3.77 mmol) was added to a solution of methyl 6-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1H-indole-2-carboxylate (1.15 g, 3.77 mmol) in DMF (6 mL) and stirred overnight. The reaction was partitioned between EtOAc and water. The organic layer was separated, dried over MgSO4, filtered and concentrated. The residue was adsorbed onto silica gel and purification was accomplished by silica gel column chromatography (EtOAc/hexanes) to afford the title compound (0.246 g, 17%). 1H NMR (400 MHz, CDCl3): δ ppm 9.31 (br. s., 1H), 7.48 (d, 1H), 6.76-6.84 (m, 2H), 3.98 (s, 3H), 0.99 (s, 9H), 0.21 (s, 6H).

Provenance & Evidence