Hydrochloric Acid → 1H-Indole, 5-methoxy-3-methyl-6-(trifluoromethyl)-
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[C:12]([F:15])([F:14])[F:13])[NH:8][C:7](C(O)=O)=[C:6]2[CH3:19].Cl>N1C2C(=CC=CC=2)C=CC=1.CCOC(C)=O.[Cu]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[C:12]([F:15])([F:13])[F:14])[NH:8][CH:7]=[C:6]2[CH3:19]Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Procedure
To a solution of 5-Methoxy-3-methyl-6-trifluoromethyl-1H-indole-2-carboxylic acid (2.0 g, 7 mmol) in 5 ml quinoline was added copper powder (50 mg), and the reaction mixture was heated to reflux for 1.5 hours. Copper powder (50 mg) was added, and the reaction mixture was refluxed for 1 hour. The reaction mixture was cooled, diluted with EtOAc, poured into 50 ml 6 N HCl, and extracted with EtOAc. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was chromatographed (10% EtOAc/Hexanes) to give 5-Methoxy-3-methyl-6-trifluoromethyl-1H-indole (850 mg, 51% ) as a solid.
Workup
- temperaturethe reaction mixture was heated
- temperatureto reflux for 1.5 hours
- temperaturethe reaction mixture was refluxed for 1 hour
- temperatureThe reaction mixture was cooled
- extractionextracted with EtOAc
- washThe combined organic layers were washed with brine
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was chromatographed (10% EtOAc/Hexanes)
Sources & evidence
- ORD record
- ord-33c19c4244b84ad2bf814b0c4aa91459
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07858632B2
Reaction notes
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