反应详情

温度

100 °C

To a 50 mL round-bottomed flask was added N-(2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide (62 mg, 150 μmol), 1-bromo-3,4-(ethylenedioxy)benzene (32 mg, 150 μmol, Aldrich, St. Louis, Mo.), dichloro 1,1′-bis(diphenylphosphino)ferrocene palladium (II) (12 mg, 15 μmol), Cesium carbonate (98 mg, 300 μmol), dioxane (1 mL), water (0.2 mL). The reaction mixture was stirred at 100° C. for 1 h. The mixture was cooled down to room temperature. The reaction mixture was diluted with saturated NH4Cl (5 mL) and extracted with EtOAc (2×30 mL). The organic extract was washed with saturated NaCl (10 mL), dried over Na2SO4, filtered and concentrated in vacuo and the residue was purified by silica gel chromatography, eluting with 30% EtOAc/hexanes to give N-(2-chloro-5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide (51 mg, 81% yield). MS (EI, pos.) calcd for C19H14ClFN2O4S: 420.0; found 420.9. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 4.32 (s, 4 H) 6.88-7.09 (m, 4 H) 7.09-7.21 (m, 2 H) 7.74-7.87 (m, 2 H) 8.12 (d, J=2.19 Hz, 1 H) 8.30 (d, J=2.34 Hz, 1 H).

1. temperatureThe mixture was cooled down to room temperature
2. extractionextracted with EtOAc (2×30 mL)
3. extractionThe organic extract
4. washwas washed with saturated NaCl (10 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 30% EtOAc/hexanes