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

HRID 2209030Notes

Reaction equation

HRID 2209030 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](SC)[C:5]2[N:10]([CH:13]([F:15])[F:14])[CH:11]=[N:12][C:4]=2[CH:3]=1.[CH:16]1C=C(Cl)C=C(C(OO)=O)C=1.[S:27]([O-:31])([O-])(=[O:29])=S.[Na+].[Na+]>C(Cl)Cl.CCOC(C)=O.O>[Cl:1][C:2]1[N:7]=[C:6]([S:27]([CH3:16])(=[O:31])=[O:29])[C:5]2[N:10]([CH:13]([F:14])[F:15])[CH:11]=[N:12][C:4]=2[CH:3]=1

Participants

7

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 1178440426-chloro-3-(difluoromethyl)-4-(methylthio)-3H-imidazo[4,5-c]pyridine

Product 1

HCID 1178440566-chloro-3-(difluoromethyl)-4-(methylsulfonyl)-3H-imidazo[4,5-c]pyridine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-chloro-3-(difluoromethyl)-4-(methylthio)-3H-imidazo[4,5-c]pyridine (431 mg, 1.73 mmol) in DCM (12 mL) was added m-CPBA (max. 77%, 1.1 g, 4.9 mmol). After stifling 4 h, saturated aqueous sodium thiosulfate (30 mL) was added and the biphasic mixture was stirred 15 min. The mixture was diluted with EtOAc (30 mL) and water (30 mL). The phases were separated, and the organic layer was washed with saturated NaHCO3 (2×50 mL), dried over Na2SO4, filtered, and concentrated to afford 6-chloro-3-(difluoromethyl)-4-(methylsulfonyl)-3H-imidazo[4,5-c]pyridine 2.63 that was used without further purification. LCMS-ESI+ (m/z): [M+H]+ calcd for C8H7ClF2N3O2S: 282.0; found: 282.0.

Workup

  1. customThe phases were separated
  2. washthe organic layer was washed with saturated NaHCO3 (2×50 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a1a447c56b8648e9bbfaba9581918809
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

Loading…