Hydrochloric Acid → HCID 59408991, compound

Participants

Reaction Steps

To a solution of (4,5-dihydro-pyrrolo[3,2,1-hi]indol-1-yl)-oxo-acetic acid methyl ester (150 mg, 0.66 mmol) and 2-(1H-indol-3-yl)-acetamide (114 mg, 0.66 mmol) in anhydrous tetrahydrofuran (10 ml) at 0° C. was added potassium tert-butoxide (2.6 ml, 2.6 mmol; 1M solution in tetrahydrofuran). The mixture was stirred at room temperature for 1 hour before concentrated hydrochloric acid (3 ml) was added and the mixture stirred for an additional 20 minutes. The mixture was poured into ethyl acetate (200 ml) washed with water (700 ml) and brine (100 ml). The organic layer was dried over anhydrous sodium sulfate and evaporated to dryness. The residue was purified by flash column chromatography (SiO2, 40% EtOAc in hexanes) to afford 3-(4,5-dihydro-pyrrolo[3,2,1-hi]indol-1-yl)-4-(1H-indol-3-yl)-pyrrole-2,5-dione as a red solid (115 mg). 400 MHz 1H NMR (DMSO-d6) δ: 11.63 (s, 1H), 10.84 (s, 1H), 7.98 (s, 1H), 7.62 (d, J=2.8 Hz, 1H), 7.42 (d, J=8.0 Hz, 1H), 7.05-7.01 (m, 2H), 6.78-6.74 (m, 2H), 6.53 (t, J=7.2 Hz, 1H), 6.08 (d, J=8.0 Hz, 1H), 4.58 (t, J=7.2 Hz, 2H), 3.71 (t, J=6.8 Hz, 2H); LCMS: 354 [M+H].

Provenance & Evidence