Potassium Carbonate → 3-[4-(benzyloxy)phenyl]-1-ethyl-6-(2,2,2-trifluoroethoxy)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

HRID 587576Notes

Reaction equation

HRID 587576 reaction equation
FC(F)(F)S([O:6][CH2:7][C:8]([F:11])([F:10])[F:9])(=O)=O.[CH2:14]([O:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]2[C:32]3=[N:33][CH:34]=[C:35](O)[CH:36]=[C:31]3[N:30]([CH2:38][CH3:39])[C:29]2=[O:40])=[CH:24][CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[Cl-].[Ca+2]>CN(C=O)C>[CH2:14]([O:21][C:22]1[CH:23]=[CH:24][C:25]([N:28]2[C:32]3=[N:33][CH:34]=[C:35]([O:6][CH2:7][C:8]([F:11])([F:10])[F:9])[CH:36]=[C:31]3[N:30]([CH2:38][CH3:39])[C:29]2=[O:40])=[CH:26][CH:27]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 5284359Calcium ChlorideHCID 585776213-[4-(benzyloxy)phenyl]-1-ethyl-6-hydroxy-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Product 1

HCID 585777333-[4-(benzyloxy)phenyl]-1-ethyl-6-(2,2,2-trifluoroethoxy)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,2,2-Trifluoroethyl trifluoromethanesulfonate (0.144 mL) was added to a solution of 3-[4-(benzyloxy)phenyl]-1-ethyl-6-hydroxy-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (300 mg) and potassium carbonate (229 mg) in DMF (5 mL) at room temperature. The mixture was stirred at ambient temperature under a dry atmosphere (CaCl2 tube) for 3 h. The mixture was quenched with water at room temperature and extracted with AcOEt. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with 15%-50% AcOEt in hexane) to give 3-[4-(benzyloxy)phenyl]-1-ethyl-6-(2,2,2-trifluoroethoxy)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (308 mg) as colorless oil.

Workup

  1. customThe mixture was quenched with water at room temperature
  2. extractionextracted with AcOEt
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (silica gel, eluted with 15%-50% AcOEt in hexane)

Sources & evidence

ORD record
ord-f2cfe7674f8d4c30ba765b7320243b8f
Source dataset
uspto-grants-2016_01
Patent number
US09226921B2

Reaction notes

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