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 → 2-(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)pyridin-8-yl)propan-2-ol

HRID 1398187Notes

Reaction equation

HRID 1398187 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:15]2[N:19]3[CH2:20][CH2:21][CH2:22][C:23]([O:29][C:30]4[CH:35]=[C:34]([F:36])[C:33]([F:37])=[C:32]([F:38])[CH:31]=4)(C(OCC)=O)[C:18]3=[N:17][N:16]=2)[CH:6]=[CH:7][C:8]=1[C:9]1[O:13][C:12]([CH3:14])=[N:11][CH:10]=1.C[Mg]Br>C1COCC1.C(OCC)(=O)C.[Cl-].[NH4+]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:15]2[N:19]3[CH2:20][CH2:21][CH2:22][C:23]([C:3]([OH:2])([CH3:4])[CH3:8])([O:29][C:30]4[CH:35]=[C:34]([F:36])[C:33]([F:37])=[C:32]([F:38])[CH:31]=4)[C:18]3=[N:17][N:16]=2)[CH:6]=[CH:7][C:8]=1[C:9]1[O:13][C:12]([CH3:14])=[N:11][CH:10]=1

Participants

6

Reactant 2

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-carboxylateHCID 178418573HCID 178418573, compound

Product 1

HCID 666042612-(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)pyridin-8-yl)propan-2-olYield 117.4%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Procedure

Under a nitrogen atmosphere, to a mixture of 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 (0.28 g) in THF (5 ml) was added methylmagnesium bromide (1M THF solution, 2.61 ml) at 0° C., and the mixture was stirred at room temperature for 4 hr. The reaction mixture was 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), and further recrystallized from ethyl acetate/hexane to give the title compound (0.16 g).

Workup

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

Sources & evidence

ORD record
ord-c16081b429b64a4a91cd235ed5f72a7e
Source dataset
uspto-grants-2014_12
Patent number
US08901309B2

Reaction notes

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