Cesium carbonate → HCID 136387344, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 1-(5((2-chloropyridin-4-yl)oxy)-6-methylpyridin-2-yl)-3-(1-(trifluoromethyl)cyclobutyl)-1H-1,2,4-triazol-5(4H)-one (0.240 g, 0.564 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.250 g, 1.202 mmol), Cs2CO3 (0.500 g, 1.535 mmol) and Pd(PPh3)4 (0.030 g, 0.026 mmol) in EtOH (20 mL) was heated at 100° C. The solvent from the reaction mixture was completely evaporated and the residue was partitioned between DCM (30 mL) and water (30 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 in vacuo, and purified by silica gel chromatography (0-40% THF/EtOAc) to provide 1-(6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)-3-(1-(trifluoromethyl)cyclobutyl)-1H-1,2,4-triazol-5(4H)-one (0.013 g, 4.6%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 12.48 (s, 1H), 8.37 (d, J=5.7 Hz, 1H), 8.26 (s, 1H), 7.97 (s, 1H), 7.91 (d, J=8.8 Hz, 1H), 7.73 (d, J=8.8 Hz, 1H), 7.20 (d, J=2.4 Hz, 1H), 6.67 (dd, J=5.7, 2.4 Hz, 1H), 3.84 (s, 3H), 2.61 (m, 4H), 2.35 (s, 3H), 2.03 (t, J=8.2 Hz, 2H); MS (ESI) m/z: 472.2 (M+H+).

Provenance & Evidence