Sodium Carbonate → Methyl 3-iodoimidazo(1,2-a)pyridine-7-carboxylate

HRID 536294Notes

Reaction equation

HRID 536294 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][C:7]([C:10]([O:12][CH3:13])=[O:11])=[CH:6][C:5]=12.[I:14]N1C(=O)CCC1=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.O>[CH3:13][O:12][C:10]([C:7]1[CH:8]=[CH:9][N:4]2[C:3]([I:14])=[CH:2][N:1]=[C:5]2[CH:6]=1)=[O:11]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 24477Sodium ThiosulfateHCID 120273N-IodosuccinimideHCID 15096964Methyl imidazo(1,2-a)pyridine-7-carboxylate

Product 1

HCID 57497695Methyl 3-iodoimidazo(1,2-a)pyridine-7-carboxylateYield 47.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl imidazo[1,2-a]pyridine-7-carboxylate (1 g, 5.68 mmol) in DMF (30 ml) was added N-iodosuccinimide (1.53 g, 1.2 equiv) and the resulting mixture was stirred for 2 h at room temperature. The thin brown slurry was diluted with water, 10% w/v sodium thiosulfate and sodium carbonate (1M) and extracted with CH2Cl2. The aqueous was further extracted with CH2Cl2. The combined organic phases were washed with brine (280 ml), dried (MgSO4) and concentrated in vacuo to give a brown residue. The residue was triturated with ether, filtered and the solid was washed ether (2×50 ml) and dried on the filter to give the product as a white solid (0.81 g). 1H NMR (400 MHz, Me-d3-OD): 8.44 (1H, d), 8.25 (1H, s), 7.88 (1H, s), 7.61 (1H, dd), 3.95 (3H, s). MS: [M+H]+ 303.

Workup

  1. extractionextracted with CH2Cl2
  2. extractionThe aqueous was further extracted with CH2Cl2
  3. washThe combined organic phases were washed with brine (280 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto give a brown residue
  7. customThe residue was triturated with ether
  8. filtrationfiltered
  9. washthe solid was washed ether (2×50 ml)
  10. customdried on the
  11. filtrationfilter

Sources & evidence

ORD record
ord-05fee83ac1864d4a9e10c3ea8aaaa4b4
Source dataset
uspto-grants-2014_10
Patent number
US08859583B2

Reaction notes

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