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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 923755Generated: October 26, 2026

Ammonium Chloride → 2-(2-ethylsulfanylphenyl)-3-methyl-6-phenyl-3H-imidazo[4,5-b]pyridine

https://huagongshe.com/reaction/923755

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAmmonium ChlorideHCID 25517—
ReactantPotassium Phosphate, TribasicHCID 62657—
ReactantPhenylboronic AcidHCID 66827—
Reactant6-bromo-2-(2-ethylsulfanylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridineHCID 67982033—
Catalyst2-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 11269872—
Solvent1,4-DioxaneHCID 31275—
Product2-(2-ethylsulfanylphenyl)-3-methyl-6-phenyl-3H-imidazo[4,5-b]pyridineHCID 86708210106.6%

Reaction Conditions

Temperature70 °C

Reaction Steps

h mixture of 6-bromo-2-(2-ethylsulfanylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (0.35 g), tripotassium phosphate (0.42 g), phenylboronic acid (0.13 g), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (0.03 g), tris(dibenzylideneacetone)palladium(0) (0.01 g), and 1,4-dioxane (3 ml) was stirred with heating at 70° C. for 2 hours, and then heated to 90° C., and stirred with heating for further 2 hours. Into the reaction mixture cooled to room temperature, 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 0.37 g of 2-(2-ethylsulfanylphenyl)-3-methyl-6-phenyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 56).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09278983B2
Source datasetuspto-grants-2016_03
ORD IDord-3524a1d26e1d4712937b32f410e86861
Source noteuspto-grants-2016_03