Sodium Thiosulfate → 6-chloro-3-methyl-4-(methylsulfonyl)-3H-imidazo[4,5-c]pyridine

HRID 2208992Notes

Reaction equation

HRID 2208992 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](SC)[C:5]2[N:10]([CH3:13])[CH:11]=[N:12][C:4]=2[CH:3]=1.[CH:14]1C=C(Cl)C=C(C(OO)=O)C=1.[O-:25][S:26]([O-:29])(=S)=O.[Na+].[Na+]>ClCCl>[Cl:1][C:2]1[N:7]=[C:6]([S:26]([CH3:14])(=[O:29])=[O:25])[C:5]2[N:10]([CH3:13])[CH:11]=[N:12][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acid2×HCID 1178434146-chloro-3-methyl-4-(methylthio)-3H-imidazo[4,5-c]pyridine

Product 1

HCID 1178428886-chloro-3-methyl-4-(methylsulfonyl)-3H-imidazo[4,5-c]pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-chloro-3-methyl-4-(methylthio)-3H-imidazo[4,5-c]pyridine 2.02 (450 mg, 2.11 mmol) in dichloromethane (16 mL) at 0° C., was added mCPBA (≦77%, 972 mg, 4.34 mmol) and mixture was warmed to room temperature. After 80 minutes, an additional 200 mg of mCPBA was added. After an additional twenty minutes, a solution of 50% saturated Na2S2O3 (aq) (20 mL) was added and reaction mixture stirred at room temperature for fifteen minutes. Layers were separated and aqueous was extracted with ethyl acetate (4×15 mL). All organic layers were combined, washed with saturated NaHCO3 (aq) (2×30 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to yield 6-chloro-3-methyl-4-(methylsulfonyl)-3H-imidazo[4,5-c]pyridine 2.04.

Workup

  1. waitAfter an additional twenty minutes
  2. customreaction mixture
  3. customLayers were separated
  4. extractionaqueous was extracted with ethyl acetate (4×15 mL)
  5. washwashed with saturated NaHCO3 (aq) (2×30 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-805407c88c194a49bb78907c01418752
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

Loading…