Potassium Carbonate → Ethyl 5-(2-acetamido-5-methylpyridin-4-yl)-3-furoate

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	Ethyl 5-bromofuran-3-carboxylate	HCID 14592142	—
Reactant	N-(5-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetamide	HCID 66749567	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	Toluene	HCID 1140	—
Product	Ethyl 5-(2-acetamido-5-methylpyridin-4-yl)-3-furoate	HCID 66748598	95.7%

Reaction Conditions

Temperature	100 °C

Reaction Steps

A mixture of ethyl 5-bromo-3-furoate (23.7 g, 108.9 mmol), N-[5-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-yl]acetamide (20.0 g, 72.5 mmol), Pd(dppf)Cl2 (5.92 g, 9.09 mmol) and K2CO3 (20.0 g, 72.5 mmol) in water (72.5 mL) and toluene (1240 mL) was allowed to stir at 100° C. under an atmosphere of nitrogen overnight. The mixture was filtered while hot and then concentrated. The residue was washed with EtOH and water and then dried to give ethyl 5-(2-acetamido-5-methylpyridin-4-yl)-3-furoate (20.0 g, 67%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08859768B2
Source dataset	uspto-grants-2014_10
ORD ID	ord-061e3c02a7994001a21a0ec0fca3d728
Source note	uspto-grants-2014_10