1H-Indazole → 2-(2,4-Difluorophenyl)-1-(2H-indazol-1-yl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol

HRID 1158996Notes

Reaction equation

HRID 1158996 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[H-].[Na+].[F:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[C:20]1([CH2:23][N:24]2[CH:28]=[N:27][CH:26]=[N:25]2)[CH2:22][O:21]1>CN(C)C=O>[F:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[C:20]([OH:21])([CH2:23][N:24]1[CH:28]=[N:27][CH:26]=[N:25]1)[CH2:22][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][NH:2]1

Participants

5

Reactant 3

HCID 92211H-IndazoleHCID 24758Sodium hydrideHCID 101309211-(2-(2,4-Difluorophenyl)-2,3-epoxypropyl)-1H-1,2,4-triazole

Product 1

HCID 686442442-(2,4-Difluorophenyl)-1-(2H-indazol-1-yl)-3-(1H-1,2,4-triazol-1-yl)propan-2-olYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of Indazole (0.27 g, 2.32 mmol) in N, N-dimethylformamide (10 ml) was slowly added sodium hydride (0.093 g, 2.32 mmol) at 0° C., followed by stirring for 30 min and then for an additional 30 min at room temperature. Then, 1-((2-(2,4-difluorophenyl)oxiran-2-yl)methyl)-1H-1,2,4-triazole (0.50 g, 2.11 mmol) was added, followed by stirring for 2 hrs at 60° C. The reaction was quenched with the addition of water (1 ml) at 0° C. Following dilution with ethyl acetate (20 ml), the reaction mixture was washed with saturated ammonium chloride solution (20 ml) and then with brine (20 ml). The organic layer was dried over anhydrous magnesium sulfate and concentrated by evaporation in a vacuum condition. The product was purified by chromatography on silica gel to give the title compound (Yield 44%).

Workup

  1. customat 0° C.
  2. waitfor an additional 30 min at room temperature
  3. stirringby stirring for 2 hrs at 60° C
  4. customThe reaction was quenched with the addition of water (1 ml) at 0° C
  5. washthe reaction mixture was washed with saturated ammonium chloride solution (20 ml)
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated by evaporation in a vacuum condition
  8. customThe product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-9e257a9ff2b34a68b5bf515e68524f44
Source dataset
uspto-grants-2010_10
Patent number
US07812045B2

Reaction notes

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