Sodium Carbonate → N-(2-chloro-5-(imidazo[1,2-a]pyrimidin-3-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

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)

Provenance & Evidence