Cesium carbonate → 6-Chloro-N-(5-(4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-yl)-[1,2,4]-triazolo[1,5-a]pyridin-8-amine

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	5-(4-(Oxetan-3-yl)piperazin-1-yl)pyridin-2-amine	HCID 86684125	—
Reactant	8-Bromo-6-chloro-(1,2,4)triazolo(1,5-a)pyridine	HCID 86684135	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	6-Chloro-N-(5-(4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-yl)-[1,2,4]-triazolo[1,5-a]pyridin-8-amine	HCID 86684134	64.8%

Reaction Conditions

Temperature	105 °C

Reaction Steps

A 25-mL single-neck round-bottomed flask equipped with a magnetic stirrer and reflux condenser was charged with 1,4-dioxane (8 mL), 108c (250 mg, 1.07 mmol), 5-(4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-amine (252 mg, 1 mmol), and cesium carbonate (700 mg, 2 mmol). Xantphos (30 mg, 0.08 mmol) and Pd2(dba)3 (55 mg, 0.08 mmol) were added, and the reaction mixture was heated at 105° C. for 3 h. After this time the reaction was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel chromatography eluting with CH2Cl2/MeOH (20:1) to afford 108d (250 mg, 60%). MS: [M+H]+ 386.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08722676B2
Source dataset	uspto-grants-2014_05
ORD ID	ord-e3337a395ce544a1b057cdf948eaa7bd
Source note	uspto-grants-2014_05