Iodine → HCID 90123714, compound

Participants

Reaction Steps

To a solution of 1-ethyl-1H-indole-5-sulfonamide (Intermediate 56, 175 mg, 0.78 mmol) in DMF (5.0 mL) was added a solution of iodine (218 mg, 0.86 mmol) in DMF (5.0 mL). KOH (109 mg, 1.95 mmol) was then added, and the resulting reaction mixture was stirred at room temperature for 24 h. The reaction mixture was then diluted with EtOAc and sat. aq. NaHSO3 solution. The organic layer was washed with sat. aq. NaCl solution, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by preparative HPLC to give the title compound (95 mg, 35%) as a pale yellow solid after lyophilization. 1H NMR (DMSO-d6) δ 7.86-7.76 (m, 2H), 7.74-7.61 (m, 2H), 7.21 (s, 2H), 4.28 (q, J=7.2 Hz, 2H), 1.36 (t, J=7.3 Hz, 3H); MS(ESI+) m/z 351.1 (M+H)+.

Provenance & Evidence