Methyl iodide → 2-acetyl-5-bromo-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-acetyl-5-bromo-N-methyl-6-(methylsulfonamido)benzofuran-3-carboxamide (150 mg, 0.38 mmol) in DMF (3 mL) was added K2CO3 (160 mg, 1.16 mmol) and MeI (164 mg, 1.16 mmol). The mixture was heated at 60° C. for 1 hour, concentrated in vacuo to remove DMF and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give crude product. The crude product was purified by column chromatography to give 2-acetyl-5-bromo-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (70 mg, yield: 45%). 1H-NMR (CDCl3, 400 MHz) δ 9.73 (s, 1H), 9.01 (s, 1H), 7.78 (s, 1H), 3.35 (s, 3H), 3.09 (s, 3H), 3.02 (d, J=4.8 Hz, 3H), 2.77 (s, 3H). MS (M+H)+: 403/405.

Provenance & Evidence