2-methylthio-5-trifluoromethyl-1H-indole → 5-(trifluoromethyl)-1H-indole

HRID 1666870Notes

Reaction equation

HRID 1666870 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]2

Participants

4

Reactant 1

HCID 210714332-methylthio-5-trifluoromethyl-1H-indole

Product 1

HCID 27630755-(trifluoromethyl)-1H-indole

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

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

  1. filtrationfilter the mixture through celite
  2. washwash the celite with ethanol (500 ml)
  3. customEvaporate the filtrate to dryness
  4. additionadd toluene (20 ml)
  5. customevaporate
  6. customdry

Sources & evidence

ORD record
ord-548fa6aad71648358d3f513c587c77db
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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