Sodium Hydroxide → 5-[5-[[3-(trifluoromethyl)benzyl]thio]-1,3,4-oxadiazol-2-yl]-1H-indazole

HRID 452682Notes

Reaction equation

HRID 452682 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[O:14][C:13]([SH:15])=[N:12][N:11]=3)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[OH-].[Na+].[F:18][C:19]([F:29])([F:28])[C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23]Cl>CN(C)C=O.C(OCC)(=O)C>[F:18][C:19]([F:28])([F:29])[C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23][S:15][C:13]1[O:14][C:10]([C:6]2[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=2)[NH:1][N:2]=[CH:3]3)=[N:11][N:12]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 697163-(Trifluoromethyl)benzyl chlorideHCID 178527939HCID 178527939, compound

Product 1

HCID 686638495-[5-[[3-(trifluoromethyl)benzyl]thio]-1,3,4-oxadiazol-2-yl]-1H-indazoleYield 74.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-(1H-indazol-5-yl)-1,3,4-oxadiazole-2-thiol (218 mg, 1.00 mmol) and 1 M aqueous sodium hydroxide solution (1.00 mL, 1.00 mmol) in N,N-dimethylformamide (5 mL) was added 3-(trifluoromethyl)benzyl chloride (0.155 mL, 1.00 mmol) at room temperature, and the resulting mixture was stirred overnight. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (tetrahydrofuran) and recrystallized from methanol to give the title compound (279 mg, yield 74%) as colorless crystals.

Workup

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by basic silica gel column chromatography (tetrahydrofuran)
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-570f80a1681649abb48b6ead548c350f
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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