反应详情

To the reaction vessel containing methyl 5-{N-[(6-amino-5-iodopyridin-3-yl)carbonyl]-S-methylsulfonimidoyl}pentanoate (2.0 g, 4.56 mmol, 1 eq), 3-ethynylaniline (0.715 mL, 1.5 eq), and bis(triphenylphosphine)palladium(II) dichloride (320 mg, 0.1 eq) in anhydrous DMF (10 mL) under anhydrous nitrogen atmosphere was added triethylamine (2.54 mL, 4 eq) and copper(I) iodide (173 mg, 0.2 eq). The reaction mixture was stirred at RT for 15 minutes and then partitioned between saturated aq NaHCO3 and EtOAc. The organic layer was separated, washed with aq NH4Cl (1×) and brine (1×), followed by drying with anhydrous Na2SO4. The upper clear liquid was decanted, concentrated, and the brown oily residue was subject twice to a gradient column chromatography (EtOAc-Hex from 1:3 to MeOH-EtOAc-Hex 1:30:6). Concentration of the product eluting fractions provided the title compound as a white foam (1.32 g, 68%).

1. custompartitioned between saturated aq NaHCO3 and EtOAc
2. customThe organic layer was separated
3. washwashed with aq NH4Cl (1×) and brine (1×)
4. dry with materialby drying with anhydrous Na2SO4
5. customThe upper clear liquid was decanted
6. concentrationconcentrated
7. washConcentration of the product eluting fractions