Cesium carbonate → 5-Bromo-1-methyl-3-(5-methyloxazol-2-ylamino)pyridin-2(1H)-one

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	3,5-Dibromo-1-methylpyridin-2(1H)-one	HCID 3614350	—
Reactant	5-Methyl-1,3-oxazol-2-amine	HCID 12495133	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	5-Bromo-1-methyl-3-(5-methyloxazol-2-ylamino)pyridin-2(1H)-one	HCID 86683966	88%

Reaction Conditions

Temperature	92 °C

Reaction Steps

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 5-methyloxazol-2-amine (276 mg, 2.82 mmol), 3,5-dibromo-1-methylpyridin-2(1H)-one (753 mg, 2.82 mmol), tris-(dibenzylideneacetone)dipalladium(0) (256 mg, 0.28 mmol), XantPhos (324 mg, 0.56 mmol), Cs2CO3 (1.8 g, 5.64 mmol), and 1,4-dioxane (30 mL). After three cycles of vacuum/argon flush, the mixture was heated at 92° C. for 3 hrs. It was then cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica-gel column chromatography eluting with 100:1 dichloromethane/methanol to afford 125a as a white solid (702 mg, 88%). MS-ESI: [M+H]+ 284.1.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08754077B2
Source dataset	uspto-grants-2014_06
ORD ID	ord-ac62a2eb66e4498588f631acebdc7529
Source note	uspto-grants-2014_06