Water → Ethyl 3-(5-(5-chloro-2-(((2',4'-dichloro-3-fluoro-[1,1'-biphenyl]-4-yl)amino)methyl)phenyl)picolinamido)propanoate

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	(2,4-Dichlorophenyl)boronic acid	HCID 2734659	—
Reactant	Ethyl 3-(5-(2-(((4-bromo-2-fluorophenyl)amino)methyl)-5-chlorophenyl)picolinamido)propanoate	HCID 71059944	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Ethyl Acetate	HCID 8857	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	Ethyl 3-(5-(5-chloro-2-(((2',4'-dichloro-3-fluoro-[1,1'-biphenyl]-4-yl)amino)methyl)phenyl)picolinamido)propanoate	HCID 71059882	—

Reaction Steps

Ethyl 3-(5-(2-(((4-bromo-2-fluorophenyl)amino)methyl)-5-chlorophenyl)picolinamido)propanoate (138 mg, 0.26 mmol), (2,4-dichlorophenyl)boronic acid (57 mg, 0.30 mmol), Pd(dppf)Cl2 (21 mg, 0.03 mmol), and K2CO3 (71 mg, 0.52 mmol) were dissolved in 1,4-dioxane (1.0 mL) and water (0.25 mL) and the resulting mixture was heated to 80° C. After 3 h the resulting mixture was cooled to room temperature, diluted with EtOAc, washed with water and brine, dried (Na2SO4), and dry packed onto silica gel. Column chromatography yielded the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08748624B2
Source dataset	uspto-grants-2014_06
ORD ID	ord-213489b3530b4c1f8b34fe19769cda88
Source note	uspto-grants-2014_06