Ethyl Acetate → 2-Ethyl-3-[[2-(1-methyl-1h-pyrazol-4-yl)-4-pyridinyl]oxy]-6-nitropyridine

Participants

Reaction Conditions

Reaction Steps

3-((2-chloropyridin-4-yl)oxy)-2-ethyl-6-nitropyridine (1.0 g, 3.6 mmol) and 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.0 g, 4.6 mmol) were dissolved in dioxane (10 mL). A solution of K2CO3 (1.5 g, 10.6 mmol) in water (2 mL) was added and the mixture was sonicated and sparged with Ar for 10 min. Pd(PPh3)4 (0.21 g, 0.18 mmol) was added and the reaction mixture was stirred at 80° C. for 24 h. EtOAc (60 mL) was added and the mixture was washed with sat. NaHCO3 (aq) (60 mL) and brine (60 mL), dried (Na2SO4), and concentrated in vacuo to afford 2-ethyl-3-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)-6-nitropyridine (1.2 g, 100%) as a brown viscous oil that was carried forward without further purification. MS (ESI) m/z: 326.1 (M+H+).

Provenance & Evidence