Potassium Carbonate → Ethyl 3-(5-(2-formyl-3,5-bis(trifluoromethyl)phenyl)picolinamido)propanoate

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	Ethyl 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamido)propanoate	HCID 71059832	—
Reactant	2-Bromo-4,6-bis(trifluoromethyl)benzaldehyde	HCID 86674259	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Dichloromethane	HCID 6344	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	Ethyl 3-(5-(2-formyl-3,5-bis(trifluoromethyl)phenyl)picolinamido)propanoate	HCID 86674260	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

2-bromo-4,6-bis(trifluoromethyl)benzaldehyde (100 mg, 0.31 mmol), ethyl 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamido)propanoate (119 mg, 0.34 mmol), Pd(dppf)Cl2 (23 mg, 0.03 mmol), and 2M K2CO3 (0.31 mL, 0.62 mmol), were dissolved in 1,4-dioxane (1.0 mL) and heated to 100° C. After 70 min the resulting mixture was cooled to room temperature, diluted with DCM, 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-bf921c0c8e4e4efc98e1e80d12b92bc1
Source note	uspto-grants-2014_06