3-Methyl-5-phenylmethoxy-1-(4-pyridinylamino)-1H-indole → 3-Methyl-1-(4-pyridinylamino)-1H-indol-5-ol

HRID 1955675Notes

Reaction equation

HRID 1955675 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11]CC3C=CC=CC=3)[CH:9]=2)[N:4]([NH:19][C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)[CH:3]=1>C(O)C.[Pd]>[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([OH:11])[CH:9]=2)[N:4]([NH:19][C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)[CH:3]=1

Participants

4

Reactant 1

HCID 190724043-Methyl-5-phenylmethoxy-1-(4-pyridinylamino)-1H-indole

Product 1

HCID 190723853-Methyl-1-(4-pyridinylamino)-1H-indol-5-olYield 31.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-Methyl-5-phenylmethoxy-1-(4-pyridinylamino)-1H-indole (2.2 g) dissolved in absolute ethanol (80 ml) was hydrogenated at 344.74 Kpa (Parr shaker, 50 psi) over ten percent palladium on carbon (0.26 g) at 50° C. for two hours. The catalyst was removed by filtration and the solids were washed with methanol. Concentration and recrystallization from methanol afforded the title compound as a solid (0.5 g), m.p. 239°-241° C. (dec.).

Workup

  1. customThe catalyst was removed by filtration
  2. washthe solids were washed with methanol
  3. concentrationConcentration and recrystallization from methanol

Sources & evidence

ORD record
ord-3352568aabc24b76a36bc2ade598f1e3
Source dataset
uspto-grants-1998_07
Patent number
US05776955

Reaction notes

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