Hydrochloric Acid → HCID 25110655, compound

Participants

Reaction Steps

To a solution of 3-(5-bromo-1H-indol-3-yl)-4-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-8-yl)-pyrrole-2,5-dione (250 mg, 0.559 mmol) in methanol (35 ml) was added magnesium turnings (354 mg, 14.57 mmol) portionwise over 20 minutes and the mixture was heated to reflux for 6 hours. The mixture was cooled and diluted with water (50 ml) and acidified with 2M aqueous hydrochloric acid. The mixture was extracted with dichloromethane (3×50 ml) and the combined organic extracts were dried over anhydrous sodium sulfate and evaporated to dryness. The residue was purified (Xterra C18, reverse phase column, eluted with acetonitrile-water system with 0.1% trifluoracetic acid as modifier) to provide (±)-trans-3-(5-bromo-1H-indol-3-yl)-4-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-8-yl)-pyrrolidine-2,5-dione as a brown solid (45 mg). M.p.=195-200° C.; 400 MHz 1H NMR (DMSO-d6) δ: 11.41 (s, 1H), 11.24 (s, 1H), 7.99 (d, J=2.0 Hz, 1H), 7.47 (d, J=2.0 Hz, 1H), 7.30 (m, 3H), 7.17 (dd, J=8.4 and 2.0 Hz, 1H), 6.83 (s, 1H), 4.53 (d, J=7.6 Hz, 1H), 4.38 (d, J=7.6 Hz, 1H), 4.13 (m, 2H), 2.90 (t, J=6.0 Hz, 2H), 2.11 (m, 2H); LCMS: 448 and 450 [M+H].

Provenance & Evidence