3-Bromo-4-fluorobenzaldehyde → 4-(3-bromo-4-fluorophenyl)-1-methyl-4,9-dihydro-1 H-isoxazolo[3,4-b]pyrano[4,3-e]pyridine-3,5(6H,8H)-dione

Participants

Reaction Steps

The product from Example 45A (0.11 g, 1 mmol), 3-bromo-4-fluoro-benzaldehyde(0.2 g, 1 mmol), and 2H-pyran-3,5(4H,6H)-dione (0.11 g, 1 mmol) in ethyl alcohol (3 mL) were heated at 80° C. for 2 days in a sealed tube. The reaction mixture was allowed to cool to ambient temperature and was evaporated under reduced pressure. The residue was chromatographed eluting with 5% ethanol/dichloromethane to provide the title compound as a white solid (0.09 g). 1H NMR (300 MHz, DMSO-d6) δ 3.27 (s, 3H), 4.05 (s, 2H), 4.57 (q, 2H), 4.78 (s, 1H), 7.28 (m, 2H), 7.54 (d, 1H), 10.77 (s, 1H); MS (ESI−) m/z 395 (M−H)−; Anal. Calcd for C16H12BrFN2O4: C, 48.63; H, 3.06; N, 7.09.

Provenance & Evidence