Potassium Carbonate → N-(3-ethyl-1-((1-ethyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-yl)-7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

A dry, 10 mL round bottom flask equipped with a reflux condenser and a nitrogen line was charged with 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (25.4 mg, 0.122 mmol), 7-bromo-N-(3-ethyl-1-((1-ethyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (50 mg, 0.102 mmol), Pd(PPh3)4 (5.9 mg, 0.005 mmol), and potassium carbonate (70 mg, 0.51 mmol). To the flask was added a water:DMF:CH3CN (1:1:4.5; 0.3:0.3:1.4 mL) mixture, and the reaction mixture was degassed under nitrogen, and heated at 80° C. for 5 hours. The cooled reaction mixture was diluted with water, the resulting suspension was extracted thoroughly with EtOAc and DCM, the combined organic extracts were dried over anhydrous sodium sulfate, and concentrated to afford the crude product. The crude product was subjected to preparative thin-layer chromatography on silica with 5% MeOH-DCM as eluent to afford 30.8 mg of product as a yellow solid. MS (ES+APCI) m/z=494 (M+H) detected

Provenance & Evidence