Chloroform → 6-bromo-2-(2-ethylsulfonylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine

HRID 923750Notes

Reaction equation

HRID 923750 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3SCC)[N:8]([CH3:20])[C:5]2=[N:6][CH:7]=1.C(Cl)(Cl)Cl.Cl[C:26]1C=CC=C(C(OO)=O)[CH:27]=1.[S:36]([O-:40])([O-])(=[O:38])=S.[Na+].[Na+]>O>[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[S:36]([CH2:26][CH3:27])(=[O:40])=[O:38])[N:8]([CH3:20])[C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 6212Chloroform2×HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 679820336-bromo-2-(2-ethylsulfanylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine

Product 1

HCID 867082056-bromo-2-(2-ethylsulfonylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 6-bromo-2-(2-ethylsulfanylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (0.20 g) and chloroform (3 ml), 3-chloroperbenzoic acid (purity: not less than 65%) (0.34 g) was added under ice-cooling, and then heated to room temperature, and stirred for 3.5 hours. Chloroform and saturated aqueous sodium thiosulfate solution were poured thereinto under ice-cooling, and stirred, and then, water was poured, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The resulting solid was washed with hexane, and dried to give 0.20 g of 6-bromo-2-(2-ethylsulfonylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 44).

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. temperatureunder ice-cooling
  4. stirringstirred
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. washThe resulting solid was washed with hexane
  10. customdried

Sources & evidence

ORD record
ord-5bd33a2738594874a80dad430491b8a5
Source dataset
uspto-grants-2016_03
Patent number
US09278983B2

Reaction notes

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