N-Iodosuccinimide → 2-Ethyl-3-iodoimidazo[1,2-a]pyridine

HRID 1916038Notes

Reaction equation

HRID 1916038 reaction equation
[I:1]N1C(=O)CCC1=O.[CH2:9]([C:11]1[N:12]=[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]2[CH:19]=1)[CH3:10]>C(#N)C>[CH2:9]([C:11]1[N:12]=[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]2[C:19]=1[I:1])[CH3:10]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 218319912-Ethylimidazo[1,2-a]pyridine

Product 1

HCID 1300548032-Ethyl-3-iodoimidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

As shown in FIG. 8, N-iodosuccinimide (8.37 g, 57.25 mmol) was added to a solution of 2-ethyl-imidazo[1,2-α]pyridine 70 (Example 27) (12.88 g, 57.25 mmol) in dry acetonitrile (100 mL) at 0° C. The reaction was warmed to room temperature and then stirred for 12 hours. The mixture was then concentrated and purified on silica gel (CombiFlash, Heptane/EtOAc elution) to afford 2-ethyl-3-iodo-imidazo[1,2-α]pyridine 72, as photosensitive yellow crystals with a yield of 5.6 g, 35%.

Workup

  1. concentrationThe mixture was then concentrated
  2. custompurified on silica gel (CombiFlash, Heptane/EtOAc elution)

Sources & evidence

ORD record
ord-577970f1637c4aceaadce2642be712d7
Source dataset
uspto-grants-2013_12
Patent number
US08618079B2

Reaction notes

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