Methyl iodide → 6-Chloro-5-iodo-2-(methylthio)-1H-imidazo[4,5-b]pyridine

HRID 929172Notes

Reaction equation

HRID 929172 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[NH:11][C:10](=[S:12])[NH:9][C:5]2=[N:6][C:7]=1[I:8].[OH-].[K+].I[CH3:16]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[NH:11][C:10]([S:12][CH3:16])=[N:9][C:5]2=[N:6][C:7]=1[I:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 866847396-Chloro-5-iodo-1H-imidazo[4,5-b]pyridine-2(3H)-thione

Product 1

HCID 895582656-Chloro-5-iodo-2-(methylthio)-1H-imidazo[4,5-b]pyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 6-chloro-5-iodo-1,3-dihydro-2H-imidazo[4,5-b]pyridine-2-thione (11.0 g, 35.3 mmol) and KOH (2.38 g, 42.4 mmol) in ethanol (200 mL) was stirred at rt for 0.5 h. Iodomethane (2.2 mL, 35.3 mmol) was then added and the reaction was allowed to stir for 1 h at rt. The ethanol was removed in vacuo and the resulting residue was partitioned between ethyl acetate (250 mL) and 2N HCl (50 mL). The ethyl acetate layer was washed with brine, dried over magnesium sulfate, filtered through a 100 g pad of silica gel and concentrated to give the desired product as a white solid. LC-MS: calculated for C2H5ClIN3S 325.56, observed m/e: 325.88 (M+H)+ (Rt 2.05/5 min).

Workup

  1. stirringto stir for 1 h at rt
  2. customThe ethanol was removed in vacuo
  3. customthe resulting residue was partitioned between ethyl acetate (250 mL) and 2N HCl (50 mL)
  4. washThe ethyl acetate layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered through a 100 g pad of silica gel
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-192b975a4b594e2dbe985661853cbf75
Source dataset
uspto-grants-2016_03
Patent number
US09290517B2

Reaction notes

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