Potassium Carbonate → Ethyl 3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-(3,4,5-trifluorophenoxy)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate

HRID 71158Notes

Reaction equation

HRID 71158 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:10])[CH:5]=[C:6]([F:9])[C:7]=1[F:8].C(=O)([O-])[O-].[K+].[K+].Cl[C:18]1([C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH2:23][CH2:22][CH2:21][N:20]2[C:24]([C:27]3[CH:32]=[CH:31][C:30]([C:33]4[O:37][C:36]([CH3:38])=[N:35][CH:34]=4)=[C:29]([O:39][CH3:40])[CH:28]=3)=[N:25][N:26]=[C:19]12>CN(C=O)C.C(OCC)(=O)C.[Cl-].[NH4+]>[CH3:40][O:39][C:29]1[CH:28]=[C:27]([C:24]2[N:20]3[CH2:21][CH2:22][CH2:23][C:18]([O:10][C:4]4[CH:3]=[C:2]([F:1])[C:7]([F:8])=[C:6]([F:9])[CH:5]=4)([C:41]([O:43][CH2:44][CH3:45])=[O:42])[C:19]3=[N:26][N:25]=2)[CH:32]=[CH:31][C:30]=1[C:33]1[O:37][C:36]([CH3:38])=[N:35][CH:34]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27779433,4,5-TrifluorophenolHCID 66604255Ethyl 8-chloro-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate

Product 1

HCID 66608678Ethyl 3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-(3,4,5-trifluorophenoxy)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylateYield 44.2%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 3,4,5-trifluorophenol (0.19 g) and potassium carbonate (0.50 g) in DMF (5 mL) was added ethyl 8-chloro-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate (0.50 g) at room temperature, and the mixture was stirred at 100° C. for 30 min. The reaction mixture was allowed to cool to room temperature, diluted with ethyl acetate and saturated aqueous ammonium chloride solution, the mixture was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (0.28 g).

Workup

  1. temperatureto cool to room temperature
  2. washthe mixture was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ee60824471aa49b2a03ff935c1066ff0
Source dataset
uspto-grants-2014_09
Patent number
US08822699B2

Reaction notes

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