Water → Methyl 2'-(((2,4'-dichloro-2'-methyl-[1,1'-biphenyl]-4-yl)amino)methyl)-2-methyl-5'-(trifluoromethyl)-[1,1'-biphenyl]-4-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	2-Methyl-4-methoxycarbonylphenylboronic acid, pinacol ester	HCID 11087024	—
Reactant	N-(2-bromo-4-(trifluoromethyl)benzyl)-2,4'-dichloro-2'-methyl-[1,1'-biphenyl]-4-amine	HCID 86674206	—
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	Methyl 2'-(((2,4'-dichloro-2'-methyl-[1,1'-biphenyl]-4-yl)amino)methyl)-2-methyl-5'-(trifluoromethyl)-[1,1'-biphenyl]-4-carboxylate	HCID 71060183	—

Reaction Steps

N-(2-bromo-4-(trifluoromethyl)benzyl)-2,4′-dichloro-2′-methyl-[1,1′-biphenyl]-4-amine, prepared as described in Example 1, (500 mg, 1.0 mmol), methyl 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (339 mg, 1.2 mmol), Pd(dppf)Cl2 (84 mg, 0.1 mmol), and K2CO3 (283 mg, 2.0 mmol) were dissolved in 1,4-dioxane (8 mL) and water (2 mL) and the resulting mixture was heated to 80° C. After 16 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	US09045389B2
Source dataset	uspto-grants-2015_06
ORD ID	ord-369894951c154bd59ee0707b83d1a640
Source note	uspto-grants-2015_06