HCID 59404400, compound → HCID 59404394, compound

Participants

Reaction Steps

To a solution of 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-5-thioxo-1,5-dihydro-pyrrol-2-one (4.7 g, 12 mmol) in MeOH (75 mL) under N2, with stirring, was added Raney nickel. The mixture was filtered under N2 and the filtrate evaporated. The residue obtained was purified by column chromatography (SiO2, EtOAc/hexanes), yielding 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-1,5-dihydro-pyrrol-2-one as an off-white solid (2.2 g, 6 mmol, 51%). 1H NMR (400 MHz, DMSO) δ: 11.33 (s, 1H), 8.19 (s, 1H), 7.55 (s, 1H), 7.37 (dd, J=8.0, 6.0 Hz, 2H), 7.30 (d, J=2.8 Hz, 1H), 7.07 (t, J=7.6 Hz, 1H), 6.90 (t, J=8.0 Hz, 1H), 6.76 (d, J=6.4 Hz, 1H), 6.62 (m, 2H), 4.53 (s, 2H), 4.20 (t, J=5.6 Hz, 2H), 2.94 (t, J=5.6 Hz, 2H), 2.17 (m, 1H), 1.17 (m, 1H); LCMS: 354 [M+H].

Provenance & Evidence