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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1401110Generated: October 31, 2026

Hydrochloric Acid → 6-Chloro-2-(4-methoxy-3,5-dimethylphenyl)oxazolo[4,5-C]pyridine

https://huagongshe.com/reaction/1401110

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
Reactant1,10-PhenanthrolineHCID 1318—
ReactantCesium carbonateHCID 10796—
ReactantN-(4,6-Dichloropyridin-3-yl)-4-methoxy-3,5-dimethylbenzamideHCID 86675964—
CatalystCopper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 24350—
SolventTetrahydrofuranHCID 8028—
Product6-Chloro-2-(4-methoxy-3,5-dimethylphenyl)oxazolo[4,5-C]pyridineHCID 71743128—

Reaction Conditions

Temperature180 °C

Reaction Steps

In a microwaveable vessel, 0.98 g of N-(4,6-dichloropyridin-3-yl)-4-methoxy-3,5-dimethylbenzamide were dissolved in 15 ml of dry tetrahydrofuran, and 29 mg of copper(I) iodide, 54 mg of 1,10-phenanthroline and 1.47 g of cesium carbonate were added. In a microwave sunthesizer, the reaction mixture was then heated at 180° C. for 3 h. For work-up, the mixture was added to 12 ml of a 0.5 M aqueous hydrochloric acid solution. The precipitated solid was filtered off with suction and the mother liquor was extracted twice with ethyl acetate. The collected organic phases were combined with the suction-filtered solid and the solvent was removed under reduced pressure. This gave 0.79 g (91%) of the product, which was reacted further without any further purification.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08907093B2
Source datasetuspto-grants-2014_12
ORD IDord-2419ef62c3e9457e8cefa041ff8bd9bf
Source noteuspto-grants-2014_12