反应详情

温度

100 °C

To a 50 mL round-bottomed flask was added 3-bromoimidazo[1,2-a]pyrimidine (58 mg, 291 μmol, Syntech, Houston, Tex.), N-(2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide (120 mg, 291 μmol), tetrakis(triphenylphosphine) palladium (34 mg, 29 μmol), aqueous sodium carbonate (2 M, 0.29 mL, 582 μmol), dioxane (3 mL). The reaction mixture was stirred at 100° C. for 5 h. The mixture was cooled down to room temperature. The reaction mixture was diluted with water (5 mL) and extracted with CH2Cl2 (5×20 mL). The organic extract was washed with saturated NaCl (5 mL), dried over Na2SO4, filtered and concentrated in vacuo and the residue was purified by silica gel chromatography, eluting with 10% MeOH/CH2Cl2 to give N-(2-chloro-5-(imidazo[1,2-a]pyrimidin-3-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide (68 mg, 58% yield). MS (ESI positive ion) m/z: calcd for C17H11ClFN5O2S: 403.0; found: 403.9 (M+1). 1H NMR (300 MHz, MeOH) δ ppm 7.23 (dd, J=6.94, 4.17 Hz, 1H) 7.25-7.36 (m, 2H) 7.84-7.94 (m, 2H) 8.04 (s, 1H) 8.28 (d, J=2.34 Hz, 1H) 8.52 (d, J=2.19 Hz, 1H) 8.70 (dd, J=4.17, 1.83 Hz, 1H) 8.94 (dd, J=6.94, 1.83 Hz, 1H)

1. temperatureThe mixture was cooled down to room temperature
2. extractionextracted with CH2Cl2 (5×20 mL)
3. extractionThe organic extract
4. washwas washed with saturated NaCl (5 mL)
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customthe residue was purified by silica gel chromatography
9. washeluting with 10% MeOH/CH2Cl2