Water → 5-[2-(4-Bromo-2-chloro-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-1-ethyl-1H-pyridin-2-one

HRID 1096002Notes

Reaction equation

HRID 1096002 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:22])[C:9]([C:15]2[CH:16]=[CH:17][C:18](=[O:21])[NH:19][CH:20]=2)([OH:14])[C:10]([F:13])([F:12])[F:11])=[C:4]([Cl:23])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:30](I)[CH3:31].O>CN(C)C(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:22])[C:9]([C:15]2[CH:16]=[CH:17][C:18](=[O:21])[N:19]([CH2:30][CH3:31])[CH:20]=2)([OH:14])[C:10]([F:13])([F:11])[F:12])=[C:4]([Cl:23])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 574213225-[2-(4-Bromo-2-chloro-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-1H-pyridin-2-one

Product 1

HCID 574213235-[2-(4-Bromo-2-chloro-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-1-ethyl-1H-pyridin-2-oneYield 85.7%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 5-[2-(4-bromo-2-chloro-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-1H-pyridin-2-one (354 mg) in N,N-dimethylacetamide (4.7 ml) were added powdered potassium carbonate (131 mg) and ethyl iodide (141 mg). The mixture was stirred at room temperature overnight. Water was added and the mixture was extracted with EtOAc. The organic phase was washed with water and dried (MgSO4). The product was purified by chromatography (SiO2, CH2Cl2/MeOH 1:0=>9:1) to give the title compound (324 mg) as a light yellow oil. MS (m/e)=438.2 [M+H+].

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. washThe organic phase was washed with water
  3. dry with materialdried (MgSO4)
  4. customThe product was purified by chromatography (SiO2, CH2Cl2/MeOH 1:0=>9:1)

Sources & evidence

ORD record
ord-d6c3c439965b4513a5f8521227832e44
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

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