Sodium Carbonate → HCID 44125257, compound

Participants

Reaction Conditions

Reaction Steps

A glass microwave reaction vessel was charged with a mixture of N-(5-bromo-2-chloropyridin-3-yl)-4-(2-hydroxypropan-2-yl)benzenesulfonamide from Step 2 (250 mg, 616 μmol), N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-b]pyridazin-2-yl)acetamide from Step 3 (223 mg, 739 μmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium dichloride (32 mg, 43 μmol, Strem Chemical, Inc., Newburyport, Mass.), sodium carbonate (131 mg, 1.2 mmol), and dioxane (3 mL). Ar was bubbled in for 1 minute, and the vessel was sealed and heated at 90° C. for 12 h. After cooled down to room temperature, the black suspension was filtered through a Celite® (diatomaceous earth) pad, and the filtercake was washed by MeOH-DCM (50%). The filtrate was concentrated in vacuo. Purification by silica gel chromatography (10 to 20% MeOH/CH2Cl2), followed by further purification by preparative HPLC (Phenomenex Synergi 4μ MAX-RP 150×21.2 mm, 40 to 90% CH3CN/H2O, 0.1% TFA, over 10 min) (Phenomenex, Torrance, Calif.) provided N-(6-(6-chloro-5-(4-(2-hydroxypropan-2-yl)phenylsulfonamido)pyridin-3-yl)imidazo[1,2-b]pyridazin-2-yl)acetamide (20 mg, 65% yield) as a yellow solid. MS (ESI positive ion) m/z: 501 (M+1). 1H NMR (400 MHz, MeOH-d6): δ ppm 1.51 (s, 6H), 2.22 (s, 3H), 7.66 (d, J=8.53 Hz, 2H), 7.71 (d, J=9.54 Hz, 1H), 7.78 (d, J=9.03 Hz, 2H), 7.98 (d, J=9.54 Hz, 1H), 8.43 (s, 1H), 8.56 (d, J=2.01 Hz, 1H), 8.78 (d, J=2.51 Hz, 1H).

Provenance & Evidence