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

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	3-Amino-5-methylisoxazole	HCID 66172	—
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	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	5-Bromo-1-methyl-3-(5-methylisoxazol-3-ylamino)pyridin-2(1H)-one	HCID 59216456	55.2%

Reaction Conditions

Temperature	100 °C

Reaction Steps

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 5-methylisoxazol-3-amine (1.0 g, 10.2 mmol), 3,5-dibromo-1-methylpyridin-2(1H)-one (4.09 g, 15.3 mmol), Pd2(dba)3 (467 mg, 0.51 mmol), Xantphos (598 mg, 1.02 mmol), Cs2CO3 (6.65 g, 20.4 mmol), and dioxane (50 mL). After three cycles of vacuum/argon flush, the reaction mixture was heated at 100° C. for 3 h. Analysis of the reaction mixture by LCMS showed completed conversion to the desired product. It was filtered when the mixture was still hot. The filtrate was cooled to room temperature and the resulting precipitate was collected by filtration to afford 129a (1.6 g, 55%) as a yellow solid. MS-ESI: [M+H]+ 284.1

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08669251B2
Source dataset	uspto-grants-2014_03
ORD ID	ord-5758c9c0c80e4f72b8e416082c355994
Source note	uspto-grants-2014_03