5-benzyloxy-6-isopropyl-1,3-dimethyl-1H-indole → 6-isopropyl-1,3-dimethyl-1H-indol-5-ol

HRID 81759Notes

Reaction equation

HRID 81759 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[CH:18]([CH3:20])[CH3:19])[N:14]([CH3:21])[CH:13]=[C:12]2[CH3:22])C1C=CC=CC=1>[Pd].CO>[CH:18]([C:17]1[CH:16]=[C:15]2[C:11]([C:12]([CH3:22])=[CH:13][N:14]2[CH3:21])=[CH:10][C:9]=1[OH:8])([CH3:20])[CH3:19]

Participants

4

Reactant 1

HCID 595987425-benzyloxy-6-isopropyl-1,3-dimethyl-1H-indole

Product 1

HCID 595985476-isopropyl-1,3-dimethyl-1H-indol-5-olYield 79.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5-Benzyloxy-6-isopropyl-1,3-dimethyl-1H-indole (0.270 g, 1.30 mmol) and Pd/C 10% (0.150 g) were added to 10 mL of methanol, and the mixture was hydrogenated in a Parr apparatus for 1.5 hours at 55 psi, at room temperature. The catalyst was removed by filtration and the solvent was removed in vacuo. The residue was purified with flash chromatography (5% ethyl acetate in hexanes) to yield 210 mg of 6-isopropyl-1,3-dimethyl-1H-indol-5-ol.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was removed in vacuo
  3. customThe residue was purified with flash chromatography (5% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-77340d9614c042b9ad3d0347af2fc2dc
Source dataset
uspto-grants-2014_09
Patent number
US08846705B2

Reaction notes

Loading…