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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 884902Generated: October 30, 2026

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

https://huagongshe.com/reaction/884902

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 numberUS08242133B2
Source datasetuspto-grants-2012_08
ORD IDord-976582d5f2ba4ce791cc18f33ca77fc7
Source noteuspto-grants-2012_08