反应详情

温度

60 °C

Bis(triphenylphosphine)palladium dichloride (15.53 mg, 0.022 mmol) was added to a solution of N-(2-chloro-5-iodopyridin-4-yl)methanesulfonamide (14) (184.0 mg, 0.553 mmol), tert-butyl 4-ethynyl-1H-pyrazole-1-carboxylate (4) (160.0 mg, 0.830 mmol), triethylamine (347 μL, 2.49 mmol) and copper iodide (6.32 mg, 0.033 mmol) in anhydrous DMF (2.0 mL). The reaction mixture was heated at 60° C. for 1 h under microwave irradiation, then partitioned between water (60 mL) and EtOAc (60 mL). The aqueous layer was extracted with more EtOAc (2×60 mL), the combined extracts were washed with brine (2×40 mL), dried (Na2SO4) and concentrated in vacuo. The resulting residue was absorbed on silica gel (2.0 g) and the free-running powder was placed on a 20 g isolute silica column. Elution with dichloromethane and 1% ethanol in dichloromethane afforded the title compound (108 mg, 49%). 1H-NMR (500 MHz, DMSO-d6) 1.61 (s, 9H), 3.48 (s, 3H), 7.12 (d, J=0.6 Hz, 1H), 7.91 (br t, J=0.5 Hz, 1H), 8.07 (d, J=0.5 Hz, 1H), 8.61 (d, J=0.5 Hz, 1H), 8.78 (d, J=0.7 Hz, 1H).

1. custompartitioned between water (60 mL) and EtOAc (60 mL)
2. extractionThe aqueous layer was extracted with more EtOAc (2×60 mL)
3. washthe combined extracts were washed with brine (2×40 mL)
4. dry with materialdried (Na2SO4)
5. concentrationconcentrated in vacuo
6. customThe resulting residue was absorbed on silica gel (2.0 g)
7. washElution with dichloromethane and 1% ethanol in dichloromethane