HCID 25165712, compound → HCID 25110676, compound

Participants

Reaction Steps

A solution of (3R,4R)-4-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-3-(1H-indol-3-yl)-5-thioxo-pyrrolidin-2-one and (3R,4R)-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-5-thioxo-pyrrolidin-2-one (0.070 g, 0.181 mmol) in methanol (15 mL) was treated with excess Raney nickel. The mixture was stirred at room temperature for 15 min. The reaction mixture was filtered over a pad of celite under N2 and the solvent removed under reduced pressure. The residue was purified by flash chromatography (ethyl acetate:methanol; 98:2) giving a mixture (1/1) of regio isomers (3R,4R)-4-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-3-(1H-indol-3-yl)-pyrrolidin-2-one and (3R,4R)-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-pyrrolidin-2-one (22 mg, 34%). 1H NMR (400 MHz, DMSO-d6) δ: 10.84 (d, J=13.6 Hz, 1H), 7.91 (brs, 1H), 7.46 (dd, J=7.7 and 13.6 Hz, 1H), 7.30-7.16 (m, 4H), 7.02 (m, 1H), 6.90 (m, 1H), 6.84-6.78 (m, 3H), 4.04 (brs, 2H), 4.0 (m, 1H), 3.72 (m, 1H), 3.35 (brs, 2H), 2.86 (brm, 2H), 2.07 (brm, 2H). LCMS: 356 [M+H].

Provenance & Evidence