N-Iodosuccinimide → Ethyl 6-iodo-3-methoxy-1-methyl-2-oxo-1,2-dihydropyridine-4-carboxylate

HRID 880029Notes

Reaction equation

HRID 880029 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:15])[N:5]([CH3:14])[CH:6]=[CH:7][C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10].C1C(=O)N([I:23])C(=O)C1>CN(C=O)C.C(Cl)Cl>[I:23][C:6]1[N:5]([CH3:14])[C:4](=[O:15])[C:3]([O:2][CH3:1])=[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:7]=1

Participants

5

Reactant 2

HCID 120273N-Iodosuccinimide2×HCID 15122761Ethyl 3-methoxy-1-methyl-2-oxo-1,2-dihydropyridine-4-carboxylate

Product 1

HCID 86730083Ethyl 6-iodo-3-methoxy-1-methyl-2-oxo-1,2-dihydropyridine-4-carboxylateYield 50.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of Intermediate 1 (101 mg, 0.478 mmol) in DMF (0.5 mL) was added NIS (108 mg, 0.478 mmol) at rt. The reaction was stirred at rt for 3 days. An additional equivalent of NIS (67 mg, 0.30 mmol) was added and the reaction mixture heated at 60° C. overnight. The reaction was allowed to cool, diluted with DCM (40 mL) and the organic portion washed with water and brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was dissolved in a small amount of DCM and charged to a 12 g silica gel cartridge which was eluted with a 25 min gradient from 0-100% EtOAc/hexane to give Intermediate 19A (81 mg, 50% yield) as a yellow solid.

Workup

  1. temperaturethe reaction mixture heated at 60° C. overnight
  2. temperatureto cool
  3. washthe organic portion washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was dissolved in a small amount of DCM
  8. additioncharged to a 12 g silica gel cartridge which
  9. washwas eluted with a 25 min gradient from 0-100% EtOAc/hexane

Sources & evidence

ORD record
ord-d22294cb9e67446b814a614de33554f1
Source dataset
uspto-grants-2015_03
Patent number
US08993557B2

Reaction notes

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