Iodoethane → Ethyl 6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxylate

HRID 559817Notes

Reaction equation

HRID 559817 reaction equation
[CH3:1][C:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[C:6](=[O:18])[C:5]([C:19]([OH:21])=[O:20])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].I[CH2:29][CH3:30]>CN1C(=O)CCC1>[CH3:1][C:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:16])([F:17])[F:15])[CH:9]=2)[C:6](=[O:18])[C:5]([C:19]([O:21][CH2:29][CH3:30])=[O:20])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 10340Sodium CarbonateHCID 117021046-Methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxylic acid

Product 1

HCID 17966910Ethyl 6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxylateYield 87.5%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A suspension of 6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxylic acid (Example 1 (b), 13.1 g, 43.9 mmol), sodium carbonate (5.2 g, 48.3 mmol) and iodoethane (10.6 g, 67.7 mmol) in NMP (60 ml) was stirred at ambient temperature for 19 h under a nitrogen atmosphere. The reaction mixture was partitioned between ethyl acetate and water. The organic phase was collected, washed with water and brine, dried over sodium sulphate, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica eluting with tert-butyl methyl ether/methanol (10:0.4) to give the title compound as a light brown solid (12.5 g, 87%).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. customThe organic phase was collected
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography on silica eluting with tert-butyl methyl ether/methanol (10:0.4)

Sources & evidence

ORD record
ord-bb86ac49084145a7a164d517e6f37131
Source dataset
uspto-grants-2011_11
Patent number
US08063073B2

Reaction notes

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