Water → HCID 22933660, compound

HRID 1269727Notes

Reaction equation

HRID 1269727 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].CI.[F:9][C:10]([F:24])([F:23])[C:11]([NH:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[NH:19][N:18]=[CH:17]2)=[O:12].O>CN(C)C=O>[F:24][C:10]([F:9])([F:23])[C:11]([N:13]([C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[NH:19][N:18]=[CH:17]2)[CH3:1])=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 17164427HCID 17164427, compound

Product 1

HCID 22933660HCID 22933660, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (415 mg, 3.00 mmol) and methyl iodide (0.20 ml, 3.21 mmol) were added to a solution of 2,2,2-trifluoro-N-(1H-indazol-5-yl)acetamide (688 mg, 3.00 mmol) in N,N-dimethylformamide (4 ml) at room temperature and stirred overnight at room temperature. Then, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol=99/1) to obtain 2,2,2-trifluoro-N-(1H-indazol-5-yl)-N-methylacetamide (466 mg, 64%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol=99/1)

Sources & evidence

ORD record
ord-6cb8497a9c564d15bfc985de89d473e5
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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