Cesium carbonate → N-(2-chloro-5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence