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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1913664Generated: October 29, 2026

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

https://huagongshe.com/reaction/1913664

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 numberUS08609705B2
Source datasetuspto-grants-2013_12
ORD IDord-65244a05612646e9821f2376f752c237
Source noteuspto-grants-2013_12