Water → (R)-1-(2-Methyl-pyridin-4-yl)-3-o-tolyl-3-(4-trimethylsilanylethynyl-phenyl)-propan-1-one

Participants

Reaction Conditions

Reaction Steps

To a solution of (R)-3-(4-bromo-phenyl)-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one (example 142, step 2, 150 mg) in piperidine (3 mL) were added under argon copper(I) iodide (3.6 mg) and tetrakis-triphenylphosphine palladium(0) (22 mg). The reaction mixture was heated at 50° C. and ethynyltrimethylsilane (480 μL) was added. The reaction mixture was stirred at 50° C. overnight. water and tert-butyl methyl ether were added, the phases were separated and the inorganic one was extracted with tert-butyl methyl ether (2×). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (15% to 50% ethyl acetate in n-heptane) to yield the title compound as a light yellow oil (105 mg, 61%), MS (ESI+): m/z=412.4 ([M+H]+).

Provenance & Evidence