N-Iodosuccinimide → Ethyl 5-iodo-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxylate

HRID 1888822Notes

Reaction equation

HRID 1888822 reaction equation
[I:1]N1C(=O)CCC1=O.[CH3:9][C:10]1[N:15]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)[C:14](=[O:26])[C:13]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:12][CH:11]=1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[I:1][C:11]1[CH:12]=[C:13]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:14](=[O:26])[N:15]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:23])[F:24])[CH:17]=2)[C:10]=1[CH3:9]

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 17966910Ethyl 6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxylate

Product 1

HCID 59455876Ethyl 5-iodo-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxylateYield 83%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

N-Iodosuccinimide (6.89 g, 30.6 mmol) was added to a solution of ethyl 6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxylate (9.9 g, 30.5 mmol) in DCM (45 ml) and TFA (38 ml) under a nitrogen atmosphere. After 19 h stirring at ambient temperature the solvent was concentrated in vacuo. Saturated aqueous sodium hydrogen carbonate solution and ethyl acetate were added to the residue to neutralize the remaining TFA. The organic phase was collected, washed with water and brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica eluting with DCM/methanol (10:0.2) to give the title compound as a yellow solid (11.4 g, 83%).

Workup

  1. concentrationwas concentrated in vacuo
  2. additionSaturated aqueous sodium hydrogen carbonate solution and ethyl acetate were added to the residue
  3. customThe organic phase was collected
  4. washwashed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography on silica eluting with DCM/methanol (10:0.2)

Sources & evidence

ORD record
ord-fb9f21be8c704267a4e9fea6403016f1
Source dataset
uspto-grants-2013_08
Patent number
US08501784B2

Reaction notes

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