To a yellow solution of 3-(4-bromophenyl)-1-(pyridazin-4-yl)-3-o-tolylpropan-1-one (example 2, step 3; 180 mg, 472 μmol) in N,N-dimethylacetamide (4 mL) were added copper(I) iodide (9 mg, 47 μmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (17.3 mg, 23.6 μmol) and (1-(tert-butoxycarbonyl)piperidin-4-yl)zinc(II) iodide solution (0.5 M in N,N-dimethylacetamide, 1.9 mL, 0.95 mmol; J. Org. Chem. 2004, 69, 5120). The reaction mixture was heated at 85° C., then after 5 h another portion of copper(I) iodide (9 mg, 47 μmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (17.3 mg, 23.6 μmol) was added, then after 1 h the reaction mixture was partitioned between sat, aq. ammonium chloride solution and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and evaporated. The residue was suspended in ethyl acetate/heptane 1:1 and insoluble material was removed by filtration. The filtrate was purified by chromatography (SiO2; ethyl acetate/heptane 1:1) to produce the title compound (66 mg, 29%). Orange foam, MS: 486.4 [M+H]+.
