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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2094418Generated: October 31, 2026

Tetrahydrofuran → 6-Chloro-2-(3-fluoropyridin-4-yl)-5-(trifluoromethyl)benzoxazole

https://huagongshe.com/reaction/2094418

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTetrahydrofuranHCID 8028—
ReactantTriphenylphosphineHCID 11776—
Reactantethyl N-ethoxycarbonyliminocarbamateHCID 220568—
Reactant3-fluoro-N-[4-chloro-2-hydroxy-5-trifluoromethylphenyl]isonicotinamideHCID 66880048—
SolventTolueneHCID 1140—
Product6-Chloro-2-(3-fluoropyridin-4-yl)-5-(trifluoromethyl)benzoxazoleHCID 6688011088.4%

Reaction Steps

To a mixture of 2.08 g of 3-fluoro-N-[4-chloro-2-hydroxy-5-(trifluoromethyl)phenyl]isonicotinamide, 13 ml of tetrahydrofuran and 1.79 g of triphenylphosphine, 2.98 g of 40% toluene solution of diethyl azodicarboxylate was added dropwise at room temperature. The reaction mixture was stirred for one hour. The reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 1.74 g of 6-chloro-2-(3-fluoropyridin-4-yl)-5-(trifluoromethyl)benzoxazole (hereinafter, referred to as “active compound 90”).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08445522B2
Source datasetuspto-grants-2013_05
ORD IDord-4463c576f4894b69978e54702886d599
Source noteuspto-grants-2013_05