HCID 131730655, compound → HCID 57405620, compound

Participants

Reaction Steps

The (rac)-trans-3-[6-(benzyloxy)-1H-indol-3-yl]-4-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)pyrrolidine-2,5-dione (500 mg, 1.05 mmol) and 10% Pd/C (10 mg) were stirred under 1 atmosphere of hydrogen in methanol (200 mL) at room temperature for 24 hours. The reaction mixture was filtered through a bed of Celite and the filtrate evaporated to dryness. The residue was purified by silica gel chromatography, eluting with 1-7% methanol in dichloromethane to afford to yield (rac)-trans-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(6-hydroxy-1H-indol-3-yl)pyrrolidine-2,5-dione (117 mg, 28%) as an off-white solid. Mp: 167-170° C.; 1H NMR (DMSO-d6) 400 MHz δ: 11.50 (bs, 1H), 10.62 (s, 1H), 7.32 (s, 1H), 7.13-7.17 (m, 3H), 6.83-6.89 (m, 2H), 6.71 (d, J=1.9 Hz, 1H), 6.48-6.52 (m, 1H), 4.46 (d, J=6.6 Hz, 1H), 4.37 (d, J=6.6 Hz, 1H), 4.01 (s, 2H), 2.89 (s, 2H), 2.09 (s, 2H); LCMS [M+H]: 386.

Provenance & Evidence