Hydrochloric Acid → HCID 59408988, compound

Participants

Reaction Steps

To a solution of 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-propionamide (249 mg, 1.1 mmol) and (1H-indol-3-yl)-oxo-acetic acid methyl ester (244 mg, 1.2 mmol) in anhydrous tetrahydrofuran (10 ml) at 0° C. was added potassium tert-butoxide (4.36 ml, 4.36 mmol; 1M in tetrahydrofuran). The mixture was allowed to warm to room temperature for 2 hours. Concentrated hydrochloric acid (4 ml) was added and the mixture stirred at room temperature for a further 30 minutes. The mixture was poured into ethyl acetate (250 ml), washed with water (750 ml) and purified by flash column chromatography (SiO2, 30 to 40% EtOAc in hexanes) to afford 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-ylmethyl)-4-(1H-indol-3-yl)-pyrrole-2,5-dione as an orange foam (226 mg). 400 MHz 1H NMR (CDCl3) δ: 8.54 (s, 1H), 7.80 (d, J=8.4 Hz, 1H), 7.53 (d, J=3.2 Hz, 1H), 7.42 (m, 1H), 7.3-7.25 (m, 1H), 7.21-7.17 (m, 1H), 7.09 (dd, J=1.6 and 7.2 Hz, 1H), 6.92-6.86 (m, 2H), 4.15-4.04 (m, 4H), 2.95 (t, J=6.4 Hz, 2H), 2.22-2.16 (m, 2H); LCMS: 382 [M+H].

Provenance & Evidence