Cesium carbonate → N-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)cyclopropanecarboxamide

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	Cyclopropanecarboxamide	HCID 80376	—
Reactant	3-((2-Chloropyridin-4-yl)oxy)-2-methyl-6-nitropyridine	HCID 90403621	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Catalyst	2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl	HCID 11155794	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	N-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)cyclopropanecarboxamide	HCID 90410595	85%

Reaction Conditions

Temperature	90 °C

Reaction Steps

A mixture of Example A3 (0.50 g, 1.882 mmol), cyclopropanecarboxamide (0.641 g, 7.53 mmol), Cs2CO3 (0.920 g, 2.82 mmol), and X-phos (0.045 g, 0.094 mmol) in dioxane (10 mL) was sparged with Ar, treated with Pd2(dba)3 (0.086 g, 0.094 mmol), sparged again with Ar and heated at 90° C. overnight. The mixture was cooled to RT, treated with EtOAc and the solids removed via filtration. The filtrate was washed with 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)cyclopropanecarboxamide (500 mg, 85%). MS (ESI) m/z: 315.1 (M+H+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09309224B2
Source dataset	uspto-grants-2016_04
ORD ID	ord-6457e0a0098e42dd84248a76174b4ece
Source note	uspto-grants-2016_04