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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 553695Generated: October 25, 2026

Sodium Bicarbonate → (4'-{4-[(R)-1-(2-Fluoro-phenyl)-ethoxycarbonylamino]-3-methyl-isoxazol-5-yl}-2'-methyl-biphenyl-4-yl)-acetic acid ethyl ester

https://huagongshe.com/reaction/553695

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium BicarbonateHCID 516892—
ReactantEthyl (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetateHCID 46737998—
Reactant[5-(4-Bromo-3-methyl-phenyl)-3-methyl-isoxazol-4-yl]carbamic acid (R)-1-(2-fluoro-phenyl)-ethyl EsterHCID 54765945—
CatalystHCID 178418476HCID 178418476—
Solvent1,2-DimethoxyethaneHCID 8071—
Product(4'-{4-[(R)-1-(2-Fluoro-phenyl)-ethoxycarbonylamino]-3-methyl-isoxazol-5-yl}-2'-methyl-biphenyl-4-yl)-acetic acid ethyl esterHCID 67352413—

Reaction Conditions

Temperature80 °C

Reaction Steps

[5-(4-Bromo-3-methyl-phenyl)-3-methyl-isoxazol-4-yl]-carbamic acid (R)-1-(2-fluoro-phenyl)-ethyl ester (0.350 g, 0.80 mmol), [4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetic acid ethyl ester (0.292 g, 0.96 mmol), and sodium bicarbonate (0.235 g, 2.8 mmol) were combined in 2:1 DME:water (11 mL), and the solution was purged with N2 for 5 minutes. Bis(triphenylphosphine)palladium(II) dichloride (0.030 g, 0.04 mmol) was added, and the reaction was stirred at 80° C. for 2 hour. After work-up, the crude material was purified by silica gel chromatography to give the title compound.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08048902B2
Source datasetuspto-grants-2011_11
ORD IDord-8c43c2d3cba24a81aadbd06233fc46f6
Source noteuspto-grants-2011_11