Sodium Carbonate → N-(2-chloro-5-(4-(1-piperidinyl)-6-quinolinyl)-3-pyridinyl)-4-fluorobenzenesulfonamid

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Reaction Steps

N-(2-chloro-5-(4-chloroquinolin-6-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide. To a 5 mL CEM microwave tube was added N-(5-bromo-2-chloropyridin-3-yl)-4-fluorobenzenesulfonamide (0.4 g, 1 mmol), 4-chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline (0.4 g, 1 mmol), sodium carbonate (2 mL, 3 mmol), Pd fibrecat PPh (Sigma-Aldrich, St. Lois, Mo.) (20% wt, 80 mg) and dioxane (3 mL). The vial was sealed and placed into CEM microwave for 20 min. at 120° C., with 100 Watts of power via Powermax. LC/MS showed a desired product mass as the major peak. The reaction mixture was partitioned between DCM/water. The aqueous layer was extracted with DCM (3×10 mL). The combined organic layers were washed with water, brine, dried over MgSO4 and concentrated. The crude product was purified using SiO2 (120 g) chromatography with hexanes:acetone=80%:20% as the solvent system to afford the product as light yellow solid (270 mg). MS (ESI pos. ion) m/z: calc'd for C20H12Cl2FN3O2S: 447.5; found: 448.3 (M+1). 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 6.99 (br. s., 1 H) 7.13-7.24 (m, 2 H) 7.60 (d, J=4.68 Hz, 1 H) 7.88 (dd, J=8.99, 4.90 Hz, 2 H) 7.97 (dd, J=8.77, 2.05 Hz, 1 H) 8.28 (d, J=8.77 Hz, 1 H) 8.33 (d, J=2.19 Hz, 1 H) 8.38 (d, J=1.90 Hz, 1 H) 8.52 (d, J=2.34 Hz, 1 H) 8.87 (d, J=4.68 Hz, 1 H).

Provenance & Evidence