Potassium Carbonate → HCID 136387347, compound

Participants

Reaction Conditions

Reaction Steps

1-(5-((2-Chloropyridin-4-yl)oxy)-6-methylpyridin-2-yl)-3-(1-methoxy-2-methylpropan-2-yl)-1H-1,2,4-triazol-5(4H)-one (0.10 g, 0.26 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.07 g, 0.33 mmol), and K2CO3 (0.09 g, 0.66 mmol) were suspended in a solution of dioxane (2.0 mL) and water (0.4 mL). The suspension was sonicated and sparged with Ar for 10 min followed by the addition of Pd(PPh3)4 (0.03 g, 0.026 mmol). The reaction mixture was stirred at 85° C. for 12 h, allowed to cool to RT, diluted with water (2.0 mL), and extracted with EtOAc (5×3 mL). The combined organics were dried (Na2SO4) and concentrated in vacuo to afford an orange oil. The residue was purified by silica gel chromatography (MeOH/DCM) to afford 3-(1-methoxy-2-methylpropan-2-yl)-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 (0.085 g, 76%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 11.93 (s, 1H), 8.37 (d, J=5.7 Hz, 1H), 8.26 (s, 1H), 7.96 (s, 1H), 7.85 (d, J=8.8 Hz, 1H), 7.69 (d, J=8.8 Hz, 1H), 7.18 (d, J=2.4 Hz, 1H), 6.65 (dd, J=5.7, 2.5 Hz, 1H), 3.84 (s, 3H), 3.39 (s, 2H), 3.25 (s, 3H), 2.33 (s, 3H), 1.24 (s, 6H); MS (ESI) m/z: 436.2 (M+H+).

Provenance & Evidence