Magnesium → HCID 25110676, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-1,5-dihydro-pyrrol-2-one (700 mg, 2 mmol), MeOH (25 mL) and magnesium turnings (963 mg, 40 mmol) was heated at 60° C. for 4 h. The reaction mixture was then allowed to cool to room temperature and evaporated. The residue was stirred in 1M HCl (70 mL) for 15 mins and extracted twice with EtOAc. The organics were evaporated and the residue purified using column chromatography (SiO2, EtOAc/MeOH). Tituration with hot EtOAc afforded (±)-trans-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-pyrrolidin-2-one as an off-white powder (190 mg, 27%). M.p.=241-243° C.; 1H NMR (400 MHz, DMSO-d6) δ: 10.86 (d, J=1.6 Hz, 1H), 7.92 (s, 1H), 7.44 (d, J=7.6 Hz, 1H), 7.33-7.23 (m, 3H), 7.17 (s, 1H), 7.03 (m, 1H), 6.90 (m, 1H), 6.86-6.78 (m, 2H), 4.03 (m, 4H), 3.81 (m, 1H), 3.31 (m, 1H), 2.87 (t, J=6.4 Hz, 2H), 2.08 (m, 2H); LCMS: 356 [M+H].

Provenance & Evidence