2-methylthio-5-trifluoromethyl-1H-indole → 5-(trifluoromethyl)-1H-indole
Reaction equation
CS[C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:7][CH:6]=2>[Ni].C(O)C>[F:15][C:12]([F:13])([F:14])[C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[NH:4][CH:3]=[CH:11]2Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
Combine moist Raney nickel (330 g), 2-methylthio-5-trifluoromethyl-1H-indole (33.8 g, 146.2 mmol) and absolute ethanol (850 ml) and stir. After 1.5 hours, filter the mixture through celite and wash the celite with ethanol (500 ml). Evaporate the filtrate to dryness, add toluene (20 ml) and evaporate and dry to give 5-trifluoromethylindole: mp=55-60° C.
Workup
- filtrationfilter the mixture through celite
- washwash the celite with ethanol (500 ml)
- customEvaporate the filtrate to dryness
- additionadd toluene (20 ml)
- customevaporate
- customdry
Sources & evidence
- ORD record
- ord-548fa6aad71648358d3f513c587c77db
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08044090B2
Reaction notes
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