Potassium Carbonate → Ethyl 3-(5-(5-chloro-2-formylphenyl)picolinamido)propanoate

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	5-Chloro-2-formylphenylboronic acid	HCID 3806952	—
Reactant	Ethyl 3-(5-bromopicolinamido)propanoate	HCID 62959749	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Dimethylformamide	HCID 6228	—
Product	Ethyl 3-(5-(5-chloro-2-formylphenyl)picolinamido)propanoate	HCID 86674246	—

Reaction Conditions

Temperature	90 °C

Reaction Steps

Ethyl 3-(5-bromopicolinamido)propanoate (2.2 g, 7.3 mmol), (5-chloro-2-formylphenyl)boronic acid (1.4 g, 7.7 mmol), Pd(dppf)Cl2 (810 mg, 1.1 mmol), and K2CO3 (2.3 g, 16.9 mmol) and PdCl2(dppf) were dissolved in wet DMF (10 mL) and the resulting mixture was heated to 90° C. After 16 h the resulting mixture was cooled to room temperature, filtered through CELITE and the filtrate was diluted with EtOAc, washed with water and sat. aqueous NaHCO3. The organic layer was dried (Na2SO4), concentrated and purified via column chromatography to yield the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08748624B2
Source dataset	uspto-grants-2014_06
ORD ID	ord-28d523e14b8342a2895a55997efc6abd
Source note	uspto-grants-2014_06