Oxygen → 2-{(E)-2-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]vinyl}-8-(2-trifluoromethylphenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-8-ol

HRID 546793Notes

Reaction equation

HRID 546793 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7](/[CH:9]=[CH:10]/[C:11]2[N:29]=[C:14]3[CH:15]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[C:25]([F:28])([F:27])[F:26])[CH2:16][CH2:17][CH2:18][N:13]3[N:12]=2)[CH:6]=[CH:5][C:4]=1[N:30]1[CH:34]=[C:33]([CH3:35])[N:32]=[CH:31]1.[H-].[Na+].[O:38]=O>CN(C=O)C>[CH3:1][O:2][C:3]1[N:8]=[C:7](/[CH:9]=[CH:10]/[C:11]2[N:29]=[C:14]3[C:15]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[C:25]([F:28])([F:27])[F:26])([OH:38])[CH2:16][CH2:17][CH2:18][N:13]3[N:12]=2)[CH:6]=[CH:5][C:4]=1[N:30]1[CH:34]=[C:33]([CH3:35])[N:32]=[CH:31]1

Participants

5

Reactant 3

HCID 977OxygenHCID 24758Sodium hydrideHCID 252130572-{(E)-2-[6-Methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]vinyl}-8-[2-(trifluoromethyl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-a]pyridine

Product 1

HCID 576091932-{(E)-2-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]vinyl}-8-(2-trifluoromethylphenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-8-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-{(E)-2-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]vinyl}-8-(2-Trifluoromethylphenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridine (50 mg) was dissolved in DMF (3 mL). Sodium hydride (containing 40% of mineral oil, 8.3 mg) was added and the reaction solution was stirred at room temperature for 10 minutes. The reaction solution was internally replaced with oxygen. The reaction solution was bubbled with oxygen and stirred for two hours. A sodium thiosulfate solution was added to the reaction solution, and the reaction solution was stirred at room temperature for 30 minutes. Ethyl acetate was added to the reaction solution and the organic layer was separated. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (carrier: Chromatorex Si; elution solvent: heptane:ethyl acetate=1:1→ethyl acetate→ethyl acetate:methanol=9:1) to obtain the title compound (10 mg). The property values of the compound are as follows.

Workup

  1. customThe reaction solution was bubbled with oxygen
  2. stirringstirred for two hours
  3. additionA sodium thiosulfate solution was added to the reaction solution
  4. stirringthe reaction solution was stirred at room temperature for 30 minutes
  5. additionEthyl acetate was added to the reaction solution
  6. customthe organic layer was separated
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue was purified by silica gel chromatography (carrier: Chromatorex Si; elution solvent: heptane:ethyl acetate=1:1→ethyl acetate→ethyl acetate:methanol=9:1)

Sources & evidence

ORD record
ord-3a35a02344e24e9bafec216bd07b8f1f
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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