Acetonitrile → 6-Chloro-5-iodo-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridine

HRID 2401144Notes

Reaction equation

HRID 2401144 reaction equation
O[O:2][S:3]([O-:5])=O.[K+].[C:7](#N)C.[Cl:10][C:11]1[CH:12]=[C:13]2[NH:20][C:19](SC)=[N:18][C:14]2=[N:15][C:16]=1[I:17]>O>[Cl:10][C:11]1[CH:12]=[C:13]2[NH:20][C:19]([S:3]([CH3:7])(=[O:5])=[O:2])=[N:18][C:14]2=[N:15][C:16]=1[I:17]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 23707502Potassium hydroxy sulfiteHCID 895582656-Chloro-5-iodo-2-(methylthio)-1H-imidazo[4,5-b]pyridine

Product 1

HCID 895582346-Chloro-5-iodo-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Oxone (20.8 g, 33.8 mmol) was added to an acetonitrile (100 mL)/water (100 mL) suspension of 6-chloro-5-iodo-2-(methysulfanyl)-1H-imidazo[4,5-b]pyridine (5.0 g, 15.4 mmol) and the reaction was allowed to stir for 18 h at rt. The suspension was filtered through a sintered glass funnel and the filtrate was partitioned between ethyl acetate and saturated sodium bisulfate. The ethyl acetate layer was washed with brine, dried over magnesium sulfate and concentrated to afford the title compound as a white solid that was used in subsequent steps without further purification. Solubility precludes purification and this was used as is. LC-MS: calculated for C7H5ClN3O2S 357.56, observed m/e: 357.07 (M+H)+ (Rt 1.36/4 min) 1H NMR δ (ppm) (DMSO-d6): 8.44 (1H, s), 3.53 (3H, s).

Workup

  1. filtrationThe suspension was filtered through a sintered glass funnel
  2. customthe filtrate was partitioned between ethyl acetate and saturated sodium bisulfate
  3. washThe ethyl acetate layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-98816a628638423f9ba5d36e2460d603
Source dataset
uspto-grants-2014_08
Patent number
US08796258B2

Reaction notes

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