Sodium Carbonate → N-(2-chloro-5-(cinnolin-6-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

(Some starting materials may be obtained from Inogent Laboratories Private Lmited, Begumpet Hyerabad, India) A glass microwave reaction vessel was charged with 6-bromocinnoline (150 mg, 0.7 mmol), N-(2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide (296 mg, 0.7 mmol), anhydrous sodium carbonate (228 mg, 2.2 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium dichloride (37 mg, 0.05 mmol) and dioxane-H2O (2:1, 3 mL). The reaction vessel was sealed and the mixture was stirred and heated at 100° C. for 1 h. Water was added in, and the suspension was filtered, the solid was air-dried. The crude was purified through a Redi-Sep® (Teledyne ISCO, Lincoln, Nebr.) pre-packed silica gel column (40 g), eluting with a gradient of 2% to 5% MeOH in CH2Cl2 to provide N-(2-chloro-5-(cinnolin-6-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide (15 mg, 5.0% yield) as a yellow solid. MS (ESI pos. ion) m/z: calc'd for C19H12ClFN4O2S:414.8.0; found: 415.0 (MH+). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.44(t, J=8.78 Hz, 2 H) 7.83 (dd, J=8.78, 5.27 Hz, 2 H) 8.24 (s, 1 H) 8.28-8.31 (m, 2 H) 8.46 (s, 1 H) 8.60 (d, J=9.03 Hz, 1 H) 8.79 (s, 1 H) 9.46 (d, J=5.52 Hz, 1 H) 10.60 (s, 1 H).

Provenance & Evidence