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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1913655Generated: October 30, 2026

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

https://huagongshe.com/reaction/1913655

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTetrahydrofuranHCID 8028—
ReactantTriphenylphosphineHCID 11776—
Reactantethyl N-ethoxycarbonyliminocarbamateHCID 220568—
ReactantN-[4-chloro-2-hydroxy-5-trifluoromethylphenyl]isonicotinamideHCID 66880038—
SolventTolueneHCID 1140—
Product6-Chloro-2-(pyridin-4-yl)-5-(trifluoromethyl)benzoxazoleHCID 6688176069.3%

Reaction Steps

To a mixture of 1.01 g of N-[4-chloro-2-hydroxy-5-(trifluoromethyl)phenyl]isonicotinamide, 10 ml of tetrahydrofuran and 0.92 g of triphenylphosphine, 1.53 g of 40% toluene solution of diethyl azodicarboxylate was added dropwise at room temperature, and the reaction mixture was stirred for two hours. The reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and the resultant crystals washed with methanol to give 0.66 g of 6-chloro-2-(pyridin-4-yl)-5-(trifluoromethyl)benzoxazole (hereinafter, referred to as “active compound 80”).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08609705B2
Source datasetuspto-grants-2013_12
ORD IDord-38688750df4649b3a52c5be15cdb24a7
Source noteuspto-grants-2013_12