Methyl acetoacetate → methyl 4-(3-bromo-4-fluorophenyl)-2-methyl-5-oxo-4,5,6,7-tetrahydro-1H-cyclopenta[b]pyridine-3-carboxylate

Participants

Reaction Steps

3-Bromo-4-fluorobenzaldehyde (3.045 g, 15 mmol), methyl acetoacetate (2.09 g, 18 mmol) and 3-aminocyclopent-2-enone (1.45 g, 15 mmol) were heated to 65° C. in methyl alcohol for 5 days. The reaction was allowed to cool to ambient temperature and the white precipitate collected, washed with methyl alcohol and dried to provide 2.29 g of the title compound. Flash chromatography (5% methyl alcohol/methylene chloride) of the filtrate provided an additional 1.46 g of the title compound.

Provenance & Evidence