3-Bromo-4-fluorobenzaldehyde → methyl 4-(3-bromo-4-fluorophenyl)-2,6-dimethyl-5-oxo-4,5,6,8-tetrahydro-1H-pyrano[3,4-b]pyridine-3-carboxylate

Participants

Reaction Steps

The product from Example 84C (1.3 g, 10 mmol), 3-bromo-4-fluorobenzaldehyde (2.4 g, 12 mmol) and methyl 3-aminocrotonate (1.2 g, 10 mmol) in ethanol (10 mL) were heated at 80° C. in a sealed tube for 60 hours. After cooling to ambient temperature, the mixture was filtered and the filtercake washed with ethanol and dried to provide the title compound. The filtrate was concentrated and chromatographed on silica gel eluting with 1% and then 2% and then 5% methanol in dichloromethane to provide additional quantities of the title compound.

Provenance & Evidence