1,3-Cyclohexanedione → HCID 178470350, compound

Participants

Reaction Steps

A mixture of 3-amino-2-ethoxycarbonyl-pyrrole (0.192 g, 1.25 mmol), 5-(6-chloro-5-fluoro-1H-benzimidazol-2-ylsulfanyl)-furan-2-carbaldehyde (0.37 g, 1.25 mmol) and 1,3-cyclohexanedione (0.14 g, 1.25 mmol) in 5 ml of 1-butanol is heated at reflux temperature for 2 hours. The reaction mixture is then concentrated under reduced pressure. The residue is resuspended in 5 ml of acetonitrile and the mixture is heated at reflux temperature for 30 minutes. The mixture is allowed to cool to room temperature and the insoluble material is collected by filtration, washed with diisopropylether (20 ml), pentane (20 ml) and dried under vacuum to yield 363 mg of 9-[5-(6-chloro-5-fluoro-1H-benzimidazol-2-ylsulfanyl)-furan-2-yl]-8-oxo-4,5,6,7,8,9-hexahydro-2H-pyrrolo[3,4-b]quinoline-3-carboxylic acid ethyl ester as a white powder. Yield=55%. Analytical LC/MS (method B): m/z=525 (negative ion mode, [M−H]−, 1 Cl present), m/z=527 (positive ion mode, [M+H]+, 1 Cl present).

Provenance & Evidence