Water → Ethyl 3-(5-(2-((2',4'-dichloro-[1,1'-biphenyl]-4-yl)carbamoyl)-4,5-difluorophenyl)picolinamido)propanoate

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
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-N-(2',4'-dichloro-[1,1'-biphenyl]-4-yl)-4,5-difluorobenzamide	HCID 71059866	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	Ethyl 3-(5-(2-((2',4'-dichloro-[1,1'-biphenyl]-4-yl)carbamoyl)-4,5-difluorophenyl)picolinamido)propanoate	HCID 71060076	—

Reaction Steps

2-Bromo-N-(2′,4′-dichloro-[1,1′-biphenyl]-4-yl)-4,5-difluorobenzamide (100 mg, 0.22 mmol), ethyl 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamido)propanoate (114 mg, 0.33 mmol), Pd(dppf)Cl2 (24 mg, 0.03 mmol), and K2CO3 (60 mg, 0.44 mmol) were dissolved in 1,4-dioxane (1 mL) and water (0.5 mL) and the resulting mixture was heated to 85° C. After 2 h the resulting mixture directly 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-c8b76a416a1a4739b67ca117f2515f2d
Source note	uspto-grants-2014_06