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

HRID 38343Notes

Reaction equation

HRID 38343 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-67bcb1dc627541d898bb0abb06b46815
Source dataset
uspto-grants-2013_09
Patent number
US08524725B2

Reaction notes

Loading…