Iodine → HCID 178515460, compound

Participants

Reaction Steps

A solution of 3-(1H-indol-7-yl)-4-(1H-indol-3-yl)-pyrrole-2,5-dione (140 mg, 0.428 mmol) and iodine (114 mg, 0.449 mmol) in dioxane (200 mL) was photolyzed with a 450 W Hanovia lamp fitted with pyrex filter for 20 minutes. The mixture was concentrated to ˜20 mL, poured into EtOAc and washed with 10% aq NaHSO3, water (3×), saturated aq NaHCO3, and brine, dried (MgSO4), filtered and concentrated onto SiO2. Flash Chromatography (30% EtOAc/hexanes) afforded the title compound as an orange powder which was dried under vacuum at 70° C. for overnight (66 mg, 47%). 1H NMR (400 MHz, DMSO-d6) 12.78 (s, 1H), 12.62 (s, 1H), 11.51 (S, 1H), 8.96 (d, J=8 Hz, 1H), 8.31 (d, J=8 Hz, 1H), 8.10 (d, J=8 Hz, 1H), 7.70–7.76 (m, 2H), 7.56 (dd, J=8, 8 Hz, 1H), 7.38 (dd, J=8, 8 Hz, 1H), 6.81 (br s, 1H). MS (electrospray, m/z) 326 (M++1), 324 (M−−1) 324. HRMS 326.0941 (M++1, calcd for C20H12N3O2 326.0930).

Provenance & Evidence