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

Participants

Role	Name	HCID	Charge
Reactant	Ethyl Acetate	HCID 8857	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole	HCID 2773987	—
Reactant	3-((2-Chloropyridin-4-yl)oxy)-2-ethyl-6-nitropyridine	HCID 90403108	—
Catalyst	HCID 178418397	HCID 178418397	—
Solvent	Water	HCID 962	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	2-Ethyl-3-[[2-(1-methyl-1h-pyrazol-4-yl)-4-pyridinyl]oxy]-6-nitropyridine	HCID 90403620	100%

Reaction Conditions

Temperature	80 °C

Reaction Steps

A mixture of Example A8 (1.10 g, 3.93 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.06 g, 5.11 mmol), K2CO3 (1.631 g, 11.80 mmol) and Pd(PPh3)4 (227 mg, 0.197 mmol) in dioxane (8 mL) and water (2 mL) was sparged with Ar and heated at 80° C. for 24 h. The mixture was cooled to RT, treated with EtOAc, washed with satd. NaHCO3, then brine, dried over Na2SO4 and concentrated to dryness to afford crude 2-ethyl-3-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)-6-nitropyridine (100% yield assumed) without further purification. MS (ESI) m/z: 326.1 (M+H+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09133183B2
Source dataset	uspto-grants-2015_09
ORD ID	ord-87378e23724f4acca452a8f83677870d
Source note	uspto-grants-2015_09