Pyridine → 3-[3-(3-Ethyl-1-methyl-2-oxo-azepan-3-yl)-phenoxy]-benzaldehyde

Participants

Reaction Steps

3-Ethyl-3-(3-hydroxy-phenyl)-1-methyl-azepan-2-one (as described in Example 8, Step B) (0.10 g, 0.4 mmol), 3-formylphenyl-boronic acid (0.12 g, 0.8 mmol), cupric acetate (0.073 g, 0.4 mmol) and powdered 4A molecular sieves (0.12 g) were combined under Ar, diluted with anhydrous CH2Cl2 (2 mL) and pyridine (0.162 mL, 2.0 mmol) and stirred at ambient temperature for 48 hrs. The reaction mixture was filtered, and the filtrated concentrated to dryness and partitioned between EtOAc and H2O. The aqueous layer was washed with EtOAc, the organics combined, washed with H2O, 10% aqueous NaOH solution, H2O, brine, and dried (Na2SO4). Filtration and concentration to dryness gave the title compound as a white solid after trituration with diethyl ether/hexane.

Provenance & Evidence