N-bromobutanimide → methyl 3-bromo-6-(methyloxy)-1H-indole-2-carboxylate

Participants

Reaction Steps

Methyl 6-(methyloxy)-1H-indole-2-carboxylate (0.10 g, 0.49 mmol) was dissolved in DMF (2 mL) then N-bromosuccinimide (0.095 g, 0.53 mmol) added and the reaction stirred for 38 h. The solvent was evaporated and the reaction mixture was purified by column chromatography (hexanes/EtOAc) to afford the title compound (0.075 g, 54%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 12.08 (s, 1H), 7.41 (d, 1H), 6.82-6.89 (m, 2H), 3.88 (s, 3H), 3.80 (s, 3H). MS: m/z 284.0 (M+1).

Provenance & Evidence