Sodium Carbonate → HCID 44609857, compound

Participants

Reaction Conditions

Reaction Steps

(Some starting materials may be obtained from Kalexsyn, Kalamazoo, Mich.) A glass microwave reaction vessel was charged with 6-bromoisoquinoline (120 mg, 0.58 mmol), N-(2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide (262 mg, 0.6 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium dichloride (32 mg, 0.04 mmol), sodium carbonate (183 mg, 1.730 mmol), and dioxane-H2O (2:1, 3 mL). The reaction mixture was sealed and heated at 100° C. for 1 h. Water was added in, and the suspension was filtered, the solid was air-dry. The crude product was chromatographed through a Redi-Sep® pre-packed silica gel column (40 g), eluting with a gradient of 2% to 5% MeOH in CH2Cl2 to provide N-(2-chloro-5-(isoquinolin-6-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide (20 mg, 8.4% yield) as a white solid. MS (ESI pos. ion) m/z: calc'd for C20H13ClFN3O2S:413.0; found: 414.0(MH+). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.44(t,J=8.80 Hz, 2 H) 7.82-7.85 (m, 2 H) 7.93 (d, J=5.87 Hz, 1 H) 8.00 (dd, J=8.61, 1.37 Hz, 1 H) 8.16 (d, J=2.15 Hz, 1 H) 8.29 (d, J=8.61 Hz, 1 H) 8.33 (s, 1 H) 8.58 (d, J=5.67 Hz, 1 H) 8.75 (s, 1 H) 9.40 (s, 1 H) 10.58 (s, 1 H).

Provenance & Evidence