Ether hydrochloride → 1-Benzyl-2-isopropyl-6-methoxy-1H-indole

HRID 40031Notes

Reaction equation

HRID 40031 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=2)[CH:10]=[C:9]1[C:19](O)([CH3:21])[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.CCOCC>CCOC(C)=O.CCO.[Pd]>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=2)[CH:10]=[C:9]1[CH:19]([CH3:21])[CH3:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 10953452Ether hydrochlorideHCID 597622752-(1-benzyl-6-methoxy-1H-indol-2-yl)propan-2-ol2×

Product 1

HCID 597624051-Benzyl-2-isopropyl-6-methoxy-1H-indole

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(1-benzyl-6-methoxy-1H-indol-2-yl)propan-2-ol (Compound 3, 1.05 g, 3.57 mmol) in EtOAc (35 ml) and EtOH (15 ml) was added 10% Pd—C (190 mg, 0.18 mmol) and HCl-Et2O (1.0 M, 1.25 ml, 1.25 mmol). The mixture was stirred under hydrogen gas (atmospheric pressure) for 1 h and was filtered. To the filtrate was added NaHCO3 (0.5 g) and H2O (0.5 ml), followed by Na2SO4 and MgSO4. This was then filtered and concentrated in vacuo to yield the crude title compound as a yellow solid.

Workup

  1. filtrationwas filtered
  2. additionTo the filtrate was added NaHCO3 (0.5 g) and H2O (0.5 ml)
  3. filtrationThis was then filtered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8ecb303fb22d4ec4a259e5a2f652ee4c
Source dataset
uspto-grants-2013_09
Patent number
US08524917B2

Reaction notes

Loading…