Acetamide → N-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)acetamide

Participants

Role	Name	HCID	Charge
Reactant	Acetamide	HCID 178	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl	HCID 11155794	—
Reactant	3-((2-Chloropyridin-4-yl)oxy)-2-methyl-6-nitropyridine	HCID 90403621	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Ethyl Acetate	HCID 8857	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	N-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)acetamide	HCID 90410470	24.4%

Reaction Conditions

Temperature	80 °C

Reaction Steps

A solution of Example A3 (1.7 g, 6.40 mmol) in dioxane (30 mL) was sparged with Ar, treated with acetamide (1.512 g, 25.6 mmol), Cs2CO3 (2.085 g, 6.40 mmol), X-Phos (0.153 g, 0.320 mmol) and Pd2(dba)3 (0.293 g, 0.320 mmol) and heated at 80° C. for 20 h. The mixture was cooled to RT, treated with EtOAc, the solids removed via filtration through diatomaceous earth and rinsed well with EtOAc. The filtrate was washed with water, then brine, dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (EtOAc/DCM) to afford N-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)acetamide (450 mg, 24%) as a light yellow solid. MS (ESI) m/z: 289.1 (M+H+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09309224B2
Source dataset	uspto-grants-2016_04
ORD ID	ord-b53558f2d76d4cf68df19e77f6d1ce44
Source note	uspto-grants-2016_04