Hydrochloric Acid → HCID 59404400, compound

Participants

Reaction Steps

To a solution of (5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-oxo-acetic acid methyl ester (3.4 g, 14 mmol) and 2-(1H-indol-3-yl)-thioacetamide (2.9 g, 15 mmol) in anhydrous THF (34 mL) at −30° C. under N2 was added dropwise 1M tBuOK in THF (42 mL, 42 mmol). The reaction mixture was allowed warm to room temperature over 2 h. The reaction mixture was cooled to 0° C. and concentrated HCl (42 mL) added slowly. The mixture was allowed warm to room temperature with stirring over 1 h before being diluted with EtOAc and water. The organics were separated, washed with brine and evaporated to yield a dark residue. The residue was purified by column chromatography (SiO2, EtOAc/hexanes). 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-5-thioxo-1,5-dihydro-pyrrol-2-one was obtained as a dark foam (4.7 g, 87%).

Provenance & Evidence