反应详情

A mixture of N-[methyl(oxo)phenyl-λ6-sulfanylidene]-5-[(trimethylsilyl)ethynyl]nicotinamide (73 mg, 0.21 mmol), tert-butyl (5-bromo-1,3-thiazol-2-yl)carbamate (74 mg, 0.27 mmol), dichlorobis(triphenylphosphine)palladium(II) (14 mg, 0.02 mmol), triphenylphosphine (2.7 mg, 0.004 mmol) and triethylamine (0.071 mL, 0.51 mmol) in 1.8 mL DMF at room temperature was degassed using vacuum and a H2/N2 (1:1) mixture and then copper(I) iodide (2 mg, 0.01 mmol) added. While stirring the mixture at room temperature, tetrabutylammonium fluoride (1.0 M in THF, 0.21 mL) was added over 2.5 minutes. After 5 minutes the reaction was heated at 60° C. for 2 hours. The reaction was partitioned between EtOAc and H2O and the EtOAc layer washed with H2O, aqueous HCl, saturated NaHCO3 solution, brine, dried with anhydrous Na2SO4 and concentrated. The brown oil was chromatographed eluting with hexane/acetone and the product containing fractions were concentrated to give the title compound as a light yellow solid (17 mg, 18%).

1. customwas degassed
2. temperatureAfter 5 minutes the reaction was heated at 60° C. for 2 hours
3. customThe reaction was partitioned between EtOAc and H2O
4. washthe EtOAc layer washed with H2O, aqueous HCl, saturated NaHCO3 solution, brine
5. dry with materialdried with anhydrous Na2SO4
6. concentrationconcentrated
7. customThe brown oil was chromatographed
8. washeluting with hexane/acetone
9. additionthe product containing fractions
10. concentrationwere concentrated