(R)-3-(4-Bromo-phenyl)-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one → HCID 66668285, compound

Participants

Reaction Conditions

Reaction Steps

(1-(tert-Butoxycarbonyl)piperidin-4-yl) zinc(II) iodide solution (0.5 M in N,N-dimethylacetamide, 2.0 mL, 1.0 mmol; preparation according to J. Org. Chem. 2004, 69, 5120) was added at room temperature under argon to a mixture of (R)-3-(4-bromophenyl)-1-(2-methylpyridin-4-yl)-3-o-tolylpropan-1-one (example 142, step 2; 200 mg, 507 μmol), copper(I) iodide (9.7 mg, 51 μmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (18.6 mg, 25.4 μmol) in N,N-dimethylacetamide (3 mL). The reaction mixture was heated at 85° C., then after 4 h partitioned between sat. aq. ammonium chloride solution and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and evaporated. Chromatography (SiO2; heptane-ethyl acetate gradient) produced the title compound (144 mg, 57%). Off-white foam, MS (ESI+): m/z=499.3 ([M+H]+).

Provenance & Evidence