Potassium Carbonate → 3-(1-ethyl-1H-pyrazol-4-yl)-6-(6-methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylsulfanyl)-quinoline

Participants

Reaction Steps

To a microwave vessel was added 3-bromo-6-(6-methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylsulfanyl)-quinoline (200 mg, 0.54 mmol), 1-ethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (149 mg, 0.67 mmol), K2CO3 (186 mg, 1.34 mmol), 1,4-dioxane (7 mL) and water (3.5 mL). The solution was degassed by bubbling nitrogen for 10 min and then Pd(dppf)2Cl2 dichloromethane (20 mg, 0.0269 mmol) was added. The microwave vessel was capped and reacted in a microwave reactor at 120° C. for 20 min. The microwave vessel was cooled and then the mixture was extracted into dichloromethane and washed with water. The volatiles were removed in vacuo and the residue absorbed onto silica gel and purified by flash chromatography (SiO2, dichloromethane:CH3OH 100:0-80:20) to obtain 3-(1-ethyl-1H-pyrazol-4-yl)-6-(6-methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylsulfanyl)-quinoline as a brown oil (7% yield).

Provenance & Evidence