Cesium carbonate → HCID 136387334, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 1-(5-((2-chloropyridin-4-yl)oxy)-6-methylpyridin-2-yl)-3-cyclobutyl-1H-1,2,4-triazol-5(4H)-one (0.300 g, 0.838 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.250 g, 1.202 mmol), Cs2CO3 (0.600 g, 1.842 mmol) and Pd(PPh3)4 (0.050 g, 0.043 mmol) in acetonitrile (20 mL) was heated at 100° C. under argon for 2 h. The solvent from the reaction mixture was completely evaporated and the residue partitioned between DCM (50 mL) and water (50 mL). The organic layer was separated and the aqueous layer saturated with solid sodium chloride and extracted with DCM (2×20 mL). The combined organics were dried, concentrated, subjected to silica gel chromatography (0-100% THF/EtOAc) to provide 3-cyclobutyl-1-(6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)-1H-1,2,4-triazol-5(4H)-one (0.055 g, 15%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 11.97 (s, 1H), 8.37 (d, J=5.7 Hz, 1H), 8.26 (s, 1H), 7.96 (s, 1H), 7.87 (d, J=8.8 Hz, 1H), 7.69 (d, J=8.8 Hz, 1H), 7.20 (d, J=2.4 Hz, 1H), 6.64 (dd, J=5.7, 2.4 Hz, 1H), 3.84 (s, 3H), 3.44 (m, 1H), 2.33 (s, 3H), 2.26 (m, 4H), 2.04 (m, 1H), 1.90 (m, 1H); MS (ESI) m/z: 404.2 (M+H+).

Provenance & Evidence