Cesium carbonate → (2-Boc-amino-pyridin-4-yl)-acetic acid ethyl ester

https://huagongshe.com/reaction/2069050

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	Tert-butylcarbamate	HCID 21252905	—
Reactant	Ethyl 2-(2-chloropyridin-4-yl)acetate	HCID 57709236	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	(2-Boc-amino-pyridin-4-yl)-acetic acid ethyl ester	HCID 53419364	51%

Reaction Conditions

Temperature	65 °C

Reaction Steps

A mixture of ethyl 2-(2-chloropyridin-4-yl)acetate (44) (15.0 g, 75.0 mmol), tert-butylcarbamate (26.4 g, 225 mmol), Pd2(dba)3 (1.719 g, 1.88 mmol), caesium carbonate (36.7 g, 113 mmol) and Xantphos® (2.17 g, 3.76 mmol) in THF (100 mL) was purged with nitrogen and was then stirred at 65° C. for 8 hr. The mixture was cooled to RT and was diluted with water and extracted with ether. The ether extracts were combined and washed with water and brine and then dried (MgSO4), and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 330 g, 5-20% EtOAc in isohexane, gradient elution) then subjected to SCX capture and release to provide the title compound (45) (12.0 g, 51%): m/z 281 (M+H)+ (ES+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08299073B2
Source dataset	uspto-grants-2012_10
ORD ID	ord-304c5b653cc14b8fb84bee22548b805f
Source note	uspto-grants-2012_10