N-Iodosuccinimide → Methyl 3-iodoimidazo[1,2-a]pyridine-8-carboxylate

HRID 1423032Notes

Reaction equation

HRID 1423032 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]2[N:7]([CH:11]=[CH:12][N:13]=2)[CH:8]=[CH:9][CH:10]=1)=[O:4].[I:14]N1C(=O)CCC1=O>C(#N)C>[CH3:1][O:2][C:3]([C:5]1[C:6]2[N:7]([C:11]([I:14])=[CH:12][N:13]=2)[CH:8]=[CH:9][CH:10]=1)=[O:4]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 15098894Methyl imidazo[1,2-a]pyridine-8-carboxylate

Product 1

HCID 57355257Methyl 3-iodoimidazo[1,2-a]pyridine-8-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of imidazo[1,2-a]pyridine-8-carboxylic acid methyl ester (3.24 g, 18.3 mmol) and N-iodosuccinimide (NIS) (4.11 g, 18.3 mmol) in acetonitrile (50 mL) is stirred at room temperature. After 2 hours, the reaction mixture is quenched with saturated aqueous Na2S2O3 and extracted with EtOAc (3×100 mL). The combined organic layers are washed with water, brine, dried over Na2SO4 and concentrated. The crude material is purified by silica gel chromatography eluting with 80% EtOAc in hexanes to afford 3-iodo-imidazo[1,2-a]pyridine-8-carboxylic acid methyl ester. Mp: 99-110° C.

Workup

  1. customthe reaction mixture is quenched with saturated aqueous Na2S2O3
  2. extractionextracted with EtOAc (3×100 mL)
  3. washThe combined organic layers are washed with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude material is purified by silica gel chromatography
  7. washeluting with 80% EtOAc in hexanes

Sources & evidence

ORD record
ord-5b7a530dc3364f0f8d5374c20e24666e
Source dataset
uspto-grants-2015_01
Patent number
US08927550B2

Reaction notes

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