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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 923765Generated: October 28, 2026

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

https://huagongshe.com/reaction/923765

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAmmoniaHCID 222—
ReactantCesium carbonateHCID 10796—
ReactantAmmonium ChlorideHCID 25517—
ReactantAcetylacetoneHCID 31261—
Reactant5-bromo-2-(2-ethylsulfanylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridineHCID 117729822—
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, 5-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 numberUS09278983B2
Source datasetuspto-grants-2016_03
ORD IDord-aa41e7e4b707412988114f56dbbf0ad9
Source noteuspto-grants-2016_03