Sodium sulfide nonahydrate → 2-(2-ethylsulfanyl-phenyl)-3-methyl-3H-imidazo[4,5-b]pyridin-6-thiol

HRID 533628Notes

Reaction equation

[CH2:1]([S:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:19]([CH3:20])[C:13]2=[N:14][CH:15]=[C:16](I)[CH:17]=[C:12]2[N:11]=1)[CH3:2].O.O.O.O.O.O.O.O.O.[S-2:30].[Na+].[Na+].O.[Cl-].[NH4+]>[Cu](I)I.CN(C=O)C>[CH2:1]([S:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:19]([CH3:20])[C:13]2=[N:14][CH:15]=[C:16]([SH:30])[CH:17]=[C:12]2[N:11]=1)[CH3:2]

Participants

Conditions

Temperature: 110 °C

Procedure

To a mixture of 2-(2-ethylsulfanyl-phenyl)-6-iodo-3-methyl-3H-imidazo[4,5-b]pyridine (430 mg), copper iodide (229 mg), and DMF (3 ml), sodium sulfide nonahydrate (721 mg) was added at room temperature. The mixture was stirred with heating at 110° C. for 6 hours. Into the reaction mixture cooled to room temperature, saturated aqueous ammonium chloride water solution was poured, and extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 85 mg of 2-(2-ethylsulfanyl-phenyl)-3-methyl-3H-imidazo[4,5-b]pyridin-6-thiol (hereinafter referred to as Present Compound 145):

Workup

additionwas added at room temperature
temperatureInto the reaction mixture cooled to room temperature
extractionextracted with ethyl acetate
dry with materialThe combined organic layer was dried over sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-5d16296af30f4d3f913f0eb9ed8fe3db
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853238B2

Reaction notes

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