Sodium Carbonate → N-(6-(5-amino-6-chloropyridin-3-yl)imidazo[1,2-b]pyridazin-2-yl)acetamide

Participants

Reaction Conditions

Reaction Steps

A glass microwave reaction vessel was charged with N-(6-chloroimidazo[1,2-b]pyridazin-2-yl)acetamide (0.05 g, 0.2 mmol, Aurigene, Bangalore, India), 2-chloro-5-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)pyridin-3-amine from Step 1 (0.07 g, 0.3 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium dichloride (0.01 g, 0.02 mmol), sodium carbonate (0.05 g, 0.5 mmol), and dioxane-H2O (4:1, 2 mL). Ar was bubbled in for 1 minute. The reaction mixture was sealed and heated at 100° C. for 2 h before cooled down to room temperature. The mixture was filtered through a Celite® (diatomaceous earth) pad, the filtercake was washed with MeOH-DCM (50%), and the filtrate was concentrated in vacuo. Purification by silica gel chromatography (10 to 50% MeOH/CH2Cl2) provided N-(6-(5-amino-6-chloropyridin-3-yl)imidazo[1,2-b]pyridazin-2-yl)acetamide (0.03 g, 42% yield) as a white solid. MS (ESI positive ion) m/z: 303 (M+1). 1H NMR (400 MHz, DMSO-d6): δ ppm 2.11 (s, 3H), 5.84 (s, 2H), 7.72 (d, J=9.39 Hz, 1H), 7.77 (d, J=2.15 Hz, 1H), 8.08 (d, J=9.39 Hz, 1H), 8.23 (d, J=2.15 Hz, 1H), 8.28 (s, 1H), 10.93 (s, 1H).

Provenance & Evidence