1,3-Cyclohexanedione, 4,4-dimethyl- → 4-(3-bromo-4-fluorophenyl)-1,6,6-trimethyl-4,7,8,9-tetrahydroisoxazolo[3,4-b]quinoline-3,5(1H,6H)-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 4,4-dimethyl-1,3-cyclohexanedione (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 evaporated under reduced pressure. The residue was chromatographed eluting with 5% ethanol/dichloromethane to yield 0.130 g of the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 0.92 (s, 3H), 1.0 (s, 3H), 1.82 (t, 2H), 2.65 (m, 2H), 3.22 (s, 3H), 4.67 (s, 1H), 7.21 (m, 2H), 7.43 (dd, 1H), 10.39 (s, 1H); MS (ESI−) m/z 419,421 (M−H)−; Anal. Calcd for C19H18BrFN2O3: C, 54.15; H, 4.27; N, 6.65.

Provenance & Evidence