7-(Benzyloxy)-3-(methylthio)indole → 7-(Benzyloxy)-1H-indole

HRID 1198520Notes

Reaction equation

HRID 1198520 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][CH:15]=[C:14]2SC)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Ni].C(OCC)(=O)C.C(O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 150540047-(Benzyloxy)-3-(methylthio)indole

Product 1

HCID 2607987-(Benzyloxy)-1H-indole

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Wet Raney nickel was added in portions to a stirred refluxing solution of 7-(benzyloxy)-3-(methylthio)indole (4.0 g, 14.9 mmol) in ethyl acetate (100 ml) and ethanol (60 ml) until all the starting material had been consumed (by RP HPLC). The mixture was filtered, the filtrate evaporated and the residue chromatographed on silica in ethyl acetate-hexane (1:8) to give a pale oil.

Workup

  1. customhad been consumed (by RP HPLC)
  2. filtrationThe mixture was filtered
  3. customthe filtrate evaporated
  4. customthe residue chromatographed on silica in ethyl acetate-hexane (1:8)
  5. customto give a pale oil

Sources & evidence

ORD record
ord-baaad24670c24651a68b3c3dd5ba3d6d
Source dataset
uspto-grants-1994_01
Patent number
US05281593

Reaction notes

Loading…