Iodoethane → 5-bromo-1-ethyl-3-(trifluoromethyl)pyridin-2(1H)-one

HRID 594080Notes

Reaction equation

HRID 594080 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[C:5]([OH:8])=[N:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:20][CH3:21]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:10])[F:11])[C:5](=[O:8])[N:6]([CH2:20][CH3:21])[CH:7]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 178517592HCID 178517592, compound

Product 1

HCID 904088165-bromo-1-ethyl-3-(trifluoromethyl)pyridin-2(1H)-oneYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a round bottom flask equipped with a stir bar and purged with nitrogen was added 5-bromo-3-(trifluoromethyl)pyridin-2-ol (1.0 equiv.), potassium carbonate (2.0 equiv.) and DMF (0.2 M). The mixture was stirred at room temperature and iodoethane (1.2 equiv.) was added via syringe. The mixture was warmed to 35° C. for 4 hours at which time LCMS indicated full conversion. The reaction was worked up by partitioning between water and ethyl acetate, the aqueous phase was extracted 3 more times with ethyl acetate, the organics were combined, washed with brine, dried with sodium sulfate, filtered and concentrated to yield 5-bromo-1-ethyl-3-(trifluoromethyl)pyridin-2(1H)-one (67%). 1H NMR (400 MHz, <cdcl3>) δ ppm 1.32-1.50 (m, 3H) 4.04 (q, J=7.17 Hz, 2H) 7.63 (br. s., 1H) 7.78 (br. s., 1H). LCMS (m/z) (M+H)=269.1/271.1, Rt=0.72 min

Workup

  1. customIn a round bottom flask equipped with a stir bar
  2. custompurged with nitrogen
  3. temperatureThe mixture was warmed to 35° C. for 4 hours at which time LCMS
  4. customby partitioning between water and ethyl acetate
  5. extractionthe aqueous phase was extracted 3 more times with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried with sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-56f1115e9b0242539b6b31d4178dbaff
Source dataset
uspto-grants-2016_01
Patent number
US09242969B2

Reaction notes

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