Cesium carbonate → HCID 59320209, compound

Participants

Reaction Steps

To a mixture of 3-bromo-6-(6-ethyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-5,7-difluoro-quinoline (86 mg, 0.2 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (0.21 mmol, 44 mg) and cesium carbonate (0.6 mmol<195 mg) in 1,4-dioxane (2 mL) at reflux was added [2-[(D-N)methyl]phenyl-c](tricyclohexylphosphine)trifluoroacetato-O-(SP-4-3)-palladium (Bedford, R. B.; Cazin, C. S. J.; Coles, S. J.; Gelbrich, T.; Horton, P. N.; Hursthouse, M. B.; Light, M. E. Organometallics 2003, 22, 987) (0.5 mol %, 0.1 μmol, 0.1 mg). After 30 min the reaction mixture was filtered through a pad of silica gel (2 g) eluting with dichloromethane/methanol (17/3, 12 mL). The filtrate was concentrated onto silica gel and purified via flash column chromatography (SiO2, CH2Cl2:CH3OH 100:0-90:10) to return the title compound as an off white solid (52 mg, 60% yield). Analytical data presented in Table 2.

Provenance & Evidence