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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 533626Generated: October 31, 2026

Ammonia → 6-amino-2-(2-ethylsulfanylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine

https://huagongshe.com/reaction/533626

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAmmoniaHCID 222—
ReactantCesium carbonateHCID 10796—
ReactantAmmonium ChlorideHCID 25517—
ReactantAcetylacetoneHCID 31261—
Reactant6-bromo-2-(2-ethylsulfanylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridineHCID 67982033—
Catalystacetylacetone copper(II)HCID 21863952—
SolventN-methyl-2-pyrrolidoneHCID 13387—
Product6-amino-2-(2-ethylsulfanylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridineHCID 68091052—

Reaction Conditions

Temperature120 °C

Reaction Steps

To a pressure-resistant reaction container, 6-bromo-2-(2-ethylsulfanylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (1.74 g), copper (II) acetylacetone (0.26 g), acetylacetone (0.50 g), cesium carbonate (3.25 g), NMP (9 ml), and 28% of aqueous ammonia (4 ml) were added, and stirred at 120° C. for 6 hours. The mixture was cooled to room temperature, and then saturated aqueous ammonium chloride solution was poured, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 1.20 g of 6-amino-2-(2-ethylsulfanylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 125).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08853238B2
Source datasetuspto-grants-2014_10
ORD IDord-1003af48215c4ea6be2263552c25a205
Source noteuspto-grants-2014_10