Sodium Bicarbonate → [1,1'-Biphenyl]-4-acetic acid, 4'-[4-[[[(1R)-1-(2-chlorophenyl)ethoxy]carbonyl]amino]-3-methyl-5-isoxazolyl]-, ethyl ester

Participants

Role	Name	HCID	Charge
Reactant	Sodium Bicarbonate	HCID 516892	—
Reactant	Ethyl (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate	HCID 46737998	—
Reactant	(R)-1-(2-chlorophenyl)ethyl (5-(4-bromophenyl)-3-methylisoxazol-4-yl)carbamate	HCID 66660466	—
Solvent	Water	HCID 962	—
Solvent	1,2-Dimethoxyethane	HCID 8071	—
Product	[1,1'-Biphenyl]-4-acetic acid, 4'-[4-[[[(1R)-1-(2-chlorophenyl)ethoxy]carbonyl]amino]-3-methyl-5-isoxazolyl]-, ethyl ester	HCID 67351643	—

Reaction Steps

[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-carbamic acid (R)-1-(2-chloro-phenyl)-ethyl ester (3.0 g, 6.9 mmol), [4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetic acid ethyl ester (2.2 g, 7.6 mmol), dichloro-bis(triphenylphosphine)palladium(II) (0.25 g, 0.35 mmol), and sodium bicarbonate (1.7 g, 20.7 mmol) were combined in DME (30 mL) and H2O (10 mL), and the reaction was stirred at 80° C. for 2 hours. After aqueous work-up, the crude material was purified by silica gel chromatography (0-40% EtOAc in hexanes) to give the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08048902B2
Source dataset	uspto-grants-2011_11
ORD ID	ord-7849c5f514f542c890c53e5b6b83aa1a
Source note	uspto-grants-2011_11