Hydrochloric Acid → HCID 59408990, compound

Participants

Reaction Steps

To a solution of 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-3-oxo-propionamide (2.0 g, 8.3 mmol) and (1H-indol-3-yl)-oxo-acetic acid methyl ester (1.8 g, 8.8 mmol) in anhydrous tetrahydrofuran (40 ml) at room temperature was added potassium tert-butoxide (26 ml, 26.0 mmol; 1M solution in tetrahydrofuran). After 45 minutes concentrated hydrochloric acid (10 ml) was added. Water (500 ml) was added to the mixture which was then extracted with ethyl acetate (350 ml). The organic layer was dried over anhydrous magnesium sulfate and evaporated to dryness. The residue obtained was sonicated with ethyl acetate (50 ml) to afford 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-carbonyl)-4-(1H-indol-3-yl)-pyrrole-2,5-dione as an orange solid (2.58 g). M.p.=>300° C.; 400 MHz 1H NMR (DMSO-d6) δ: 11.99 (s, 1H), 11.12 (s, 1H), 8.18 (s, 1H), 8.13 (s, 1H), 7.93 (m, 1H), 7.52 (d, J=8.0 Hz, 1H), 7.40 (d, J=8.4 Hz, 1H), 7.18 (m, 1H), 7.06-7.01 (m, 2H), 6.85 (m, 1H), 4.11 (m, 2H), 2.90 (m, 2H), 2.08 (m, 2H); LCMS: 396 [M+H].

Provenance & Evidence