Potassium Carbonate → N-(2-Chloro-5-(3-chloroquinoxalin-6-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

To a 5 mL microwave vial, 7-bromo-2-chloroquinoxaline (0.100 g, 0.410 mmol), N-(2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide (0.189 g, 0.457 mmol), dichlorobis(di-tert-butylphenylphosphine)palladium(II) (0.0138 g, 0.0222 mmol) and potassium carbonate (0.513 ml, 1.03 mmol) were mixed into 1,4-dioxane (4 mL). The mixture was degassed by bubbling nitrogen through for 5 min. The reaction mixture was stirred at 90° C. for 1.5 h. The reaction mixture was partitioned between water (20 mL) and EtOAc (20 mL). The aqueous phase was extracted with EtOAc (2×20 mL). The combined organic phases were washed with saturated aqueous NaCl (40 mL). The organic phase was dried over sodium sulfate, filtered and concentrated in vacuo. Upon addition of DCM, precipitate came out and it was collected via filtration to afford a white solid (0.0746 g) as the desired product. The filtrate was purified by silica gel column chromatography (eluent: EtOAc in hexanes 0%-50%) to afford another 0.0512 g of the product. The combine yield was 0.1258 g. MS (ESI pos. ion) m/z calcd for C19H11C12FN4O2S: 448.0; found 448.8 [M+1]. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.38-7.50 (m, 2 H) 7.79-7.89 (m, 2 H) 8.18-8.35 (m, 3 H) 8.40 (d, J=1.75 Hz, 1 H) 8.80 (d, J=2.34 Hz, 1 H) 9.05 (s, 1 H) 10.56 (br. s., 1 H).

Provenance & Evidence