HCID 59170319, compound → 1-Benzyl-2-methyl-1H-indol-4-ol

HRID 1445910Notes

Reaction equation

HRID 1445910 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[C:12]([O:17]CC3C=CC=CC=3)[CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[CH3:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.C(OCC)(=O)C.[Pd]>[CH2:1]([N:8]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([OH:17])[C:11]=2[CH:10]=[C:9]1[CH3:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 59170319HCID 59170319, compound

Product 1

HCID 107523601-Benzyl-2-methyl-1H-indol-4-ol

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-Benzyl-4-benzyloxy-2-methyl-1H-indole (2) (35 g, 0.107 mole) in methanol (1 L) and ethyl acetate (500 mL), Pd/C (10%, 17 g) was added. Hydrogen was bubbled through the mixture at room pressure and temperature for 6 h. The reaction mixture was filtered through Celite. The filtrate was concentrated and the residue was purified by column chromatography (6:1 Hex:EtOAc) to afford intermediate (3) as an orange solid. Yield: 22 g (60%)

Workup

  1. customHydrogen was bubbled through the mixture at room pressure and temperature for 6 h
  2. filtrationThe reaction mixture was filtered through Celite
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by column chromatography (6:1 Hex:EtOAc)

Sources & evidence

ORD record
ord-a9dd3908b1c941d6b24a61959aa184e8
Source dataset
uspto-grants-2010_02
Patent number
US07666898B2

Reaction notes

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