Ethyl Acetate → HCID 136387297, compound

Participants

Reaction Conditions

Reaction Steps

1-(5-((2-Chloropyridin-4-yl)oxy)-6-methylpyridin-2-yl)-3-(tert-pentyl)-1H-1,2,4-triazol-5(4H)-one (0.15 g, 0.40 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.11 g, 0.52 mmol), and K2CO3 (0.14 g, 1.04 mmol) were suspended in dioxane (1.7 mL) and water (0.33 mL). The suspension was sonicated and sparged with Ar for 10 min. Pd(PPh3)4 (0.046 g, 0.040 mmol) was added and the reaction mixture was stirred at 85° C. for 12 h. EtOAc (15 mL) was added and the suspension was filtered through a pad of diatomaceous earth. The filter cake was washed with EtOAc (3×5 mL) and the combined filtrates were concentrated in vacuo. The residue was purified by silica gel chromatography (MeOH/DCM). Product was isolated as a colorless oil that was dissolved in MeCN/water, frozen to −78° C., and lyophilized to afford 1-(6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)-3-(tert-pentyl)-1H-1,2,4-triazol-5(4H)-one (0.143 g, 79%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 11.91 (s, 1H), 8.37 (d, J=5.7 Hz, 1H), 8.25 (s, 1H), 7.96 (s, 1H), 7.86 (d, J=8.7 Hz, 1H), 7.68 (d, J=8.7 Hz, 1H), 7.18 (s, 1H), 6.66 (d, J=5.6 Hz, 1H), 3.84 (s, 3H), 2.33 (s, 3H), 1.61 (q, J=7.6 Hz, 2H), 1.23 (s, 6H), 0.76 (t, J=7.3 Hz, 3H); MS (ESI) m/z: (M+H+).

Provenance & Evidence