1,3-Cyclohexanedione → HCID 178470355, compound

Participants

Reaction Steps

A mixture of 3-amino-2-ethoxycarbonyl-pyrrole (0.412 g, 2.67 mmol), 5-[5-(tert-butyl-dimethyl-silanyloxy)-1H-benzimidazol-2-ylsulfanyl]-furan-2-carbaldehyde (1.0 g, 2.67 mmol) and 1,3-cyclohexanedione (0.299 g, 2.67 mmol) in 10 ml of 1-butanol is heated at reflux temperature for 4 hours. The reaction mixture is then concentrated under reduced pressure. The residue is purified on a silica gel column (50 g) eluted successively with cyclohexane/ethyl acetate (9/1, v/v) and cyclohexane/ethyl acetate (7/3, v/v) to yield 376 mg of 9-{5-[5-(tert-butyl-dimethyl-silanyloxy)-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 an orange solid. Yield=23%. Analytical LC/MS (method B): retention time=4.68 min., m/z=605.11 (positive ion mode).

Provenance & Evidence