Sodium Thiosulfate → HCID 68091064, compound

HRID 923782Notes

Reaction equation

HRID 923782 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:20]([CH3:21])[C:11]3=[N:12][CH:13]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:15]=[C:10]3[N:9]=2)=[C:4]([S:22][CH2:23][CH3:24])[CH:3]=1.Cl[C:26]1C=CC=C(C(OO)=[O:33])[CH:27]=1.C(=O)([O-])O.[Na+].[S:41]([O-:45])([O-])(=[O:43])=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:20]([CH3:21])[C:11]3=[N:12][CH:13]=[C:14]([C:16]([F:18])([F:19])[F:17])[CH:15]=[C:10]3[N:9]=2)=[C:4]([S:22]([CH2:23][CH3:24])=[O:33])[CH:3]=1.[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:20]([CH3:21])[C:11]3=[N:12][CH:13]=[C:14]([C:16]([F:18])([F:19])[F:17])[CH:15]=[C:10]3[N:9]=2)=[C:4]([S:41]([CH2:26][CH3:27])(=[O:45])=[O:43])[CH:3]=1

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 68091063HCID 68091063, compound

Product 2

HCID 68091064HCID 68091064, compoundHCID 68091210HCID 68091210, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of 2-(4-bromo-2-ethylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (0.40 g) and chloroform (5 ml), 3-chloroperbenzoic acid (purity: not less than 65%, 0.29 g) was added under ice-cooling, then heated to room temperature, and stirred for 2 hours. Into the reaction mixture, saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium thiosulfate solution were poured, and extracted with chloroform. The combined organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.26 g of 2-(4-bromo-2-ethylsulfinylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter, Present Compound 239) and 0.17 g of 2-(4-bromo-2-ethylsulfonylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter, Present Compound 240).

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. extractionextracted with chloroform
  4. dry with materialThe combined organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5e89ac4eb119429f9d40af698207bf21
Source dataset
uspto-grants-2016_03
Patent number
US09278983B2

Reaction notes

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