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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 231533Generated: October 26, 2026

Imidazo(4,5-b)pyridine → 6-Chloro-2-(4-chlorophenyl)-8-methoxyimidazo[1,2-a]-pyridine

https://huagongshe.com/reaction/231533

Reaction equation

Participants

RoleNameHCIDCharge
ReactantImidazo(4,5-b)pyridineHCID 67504—
ReactantSodiumHCID 5360545—
ReactantSodium MethoxideHCID 10942334—
Reactant8-Bromo-6-chloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridineHCID 14234917—
SolventMethanolHCID 887—
SolventWaterHCID 962—
SolventHexamethylphosphoramideHCID 12679—
Product6-Chloro-2-(4-chlorophenyl)-8-methoxyimidazo[1,2-a]-pyridineHCID 14234923—

Reaction Steps

10 g (29.4 mmol) of 8-bromo-6-chloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridine, the preparation of which compound is described in the patent application filed this day entitled: Derives d'imidazopyridines, leur preparation et leur application en therapeutique (Imidazopyridine derivatives, their preparation and their application in therapy) by the Applicant, dissolved in 60 ml of hexamethylphosphorotriamide, are added to a solution of sodium methylate prepared using 2.03 g of sodium and 15 ml of methanol, the reaction mixture is brought to 60° C. for 2 h 30 min., water is added, the mixture is extracted with CH2Cl2, the organic phase is washed with water, dried over MgSO4 and filtered, and the filtrate is concentrated under reduced pressure. The evaporation residue is recrystallized in an ethyl acetate/hexane mixture. M.p. 150°-151° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04847263
Source datasetuspto-grants-1989_07
ORD IDord-036eebe4c5f849078205be171443b810
Source noteuspto-grants-1989_07