Sodium Thiosulfate → HCID 71246869, compound

HRID 1473929Notes

Reaction equation

[CH2:1]([S:3]([C:6]1[C:7]([C:12]2[N:25]([CH3:26])[C:15]3=[N:16][CH:17]=[C:18]([S:20][C:21]([F:24])([F:23])[F:22])[CH:19]=[C:14]3[N:13]=2)=[N:8][CH:9]=[CH:10][CH:11]=1)(=[O:5])=[O:4])[CH3:2].ClC1C=CC=C(C(OO)=[O:35])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[CH2:1]([S:3]([C:6]1[C:7]([C:12]2[N:25]([CH3:26])[C:15]3=[N:16][CH:17]=[C:18]([S:20]([C:21]([F:24])([F:22])[F:23])=[O:35])[CH:19]=[C:14]3[N:13]=2)=[N:8][CH:9]=[CH:10][CH:11]=1)(=[O:5])=[O:4])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of 2-(3-ethylsulfonyl-pyridin-2-yl)-3-methyl-6-trifluoromethylsulfanyl-3H-imidazo[4,5-b]pyridine (500 mg) and chloroform (10 ml) was added m-chloroperbenzoic acid (purity: not less than 65%) (429 mg) while ice-cooling, and the mixture was stirred at room temperature for 1 hour and at 50° C. for 2 hours. To the reaction mixture were poured aqueous sodium thiosulfate solution and aqueous sodium hydrogen carbonate solution, and the mixture was extracted with chloroform. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2-(3-ethylsulfonyl-pyridin-2-yl)-3-methyl-6-trifluoromethylsulfinyl-3H-imidazo[4,5-b]pyridine (353 mg), which is hereinafter referred to as “the present compound 20”.

Workup

temperaturecooling
extractionthe mixture was extracted with chloroform
dry with materialThe organic layer was dried over sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-5e270535cabd4cd7861c1560e339d3e9
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018134B2

Reaction notes

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