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

https://huagongshe.com/reaction/2069064

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	HCID 58532559	HCID 58532559	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	(2-Boc-amino-pyridin-4-yl)-acetic acid ethyl ester	HCID 53419364	852.7%

Reaction Conditions

Temperature	65 °C

Reaction Steps

A mixture of ethyl 2-(2-chloropyridin-4-yl)-2-methylpropanoate (57) (2.80 g, 12.3 mmol), tert-butylcarbamate (4.32 g, 36.9 mmol), Pd2(dba)3 (281 mg, 0.307 mmol), Xantphos (355 mg, 0.615 mmol) and caesium carbonate (6.01 g, 18.5 mmol) in THF (10.0 mL) was purged with nitrogen and then stirred at 65° C. for 72 hr. The mixture was cooled to RT and was diluted with water and extracted with ether. The organic layer was washed with water and brine and then dried (MgSO4), and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 120 g, 5-8% EtOAc in isohexane, gradient elution) to give the title compound (58) (1.47 g, 37%): m/z 309 (M+H)+ (ES+)

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08299073B2
Source dataset	uspto-grants-2012_10
ORD ID	ord-1d684c10cc124a7394299e38812c64b3
Source note	uspto-grants-2012_10