8-Hydroxyquinoline → 3-(1H-1,2,4-triazol-1-yl)-5-(trifluoromethyl)pyridin-2-amine
Reaction equation
I[C:2]1[C:3]([NH2:12])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[NH:13]1[CH:17]=[N:16][CH:15]=[N:14]1.N1C2C(=CC=CC=2O)C=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.[Cu]I.CS(C)=O>[N:13]1([C:2]2[C:3]([NH2:12])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=2)[CH:17]=[N:16][CH:15]=[N:14]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 120 °C
Procedure
A mixture of 3-iodo-5-(trifluoromethyl)pyridin-2-amine (5.0 g), 1,2,4-triazole (1.44 g), copper(I) iodide (0.496 g), 8-quinolinol (0.378 g), potassium carbonate (2.88 g) and DMSO (50 mL) was stirred at 120° C. for 7 hr under nitrogen gas atmosphere. The reaction solution was allowed to be cooled to room temperature, diluted with ethyl acetate, and filtered through basic silica gel column (ethyl acetate). The filtrate was washed successively with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified successively by silica gel column chromatography (ethyl acetate/hexane) and silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (2.4 g).
Workup
- temperatureto be cooled to room temperature
- filtrationfiltered through basic silica gel column (ethyl acetate)
- washThe filtrate was washed successively with water and saturated brine
- dry with materialdried over anhydrous sodium sulfate
- customthe solvent was evaporated under reduced pressure
- customThe residue was purified successively by silica gel column chromatography (ethyl acetate/hexane) and silica gel column chromatography (NH, ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-fdb5187cb8fe4cf8ae44adadac2dc757
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09296746B2
Reaction notes
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