HCID 86686447, compound → HCID 86686448, compound

HRID 2176811Notes

Reaction equation

HRID 2176811 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH:18]([CH2:20][CH2:21][CH3:22])[CH3:19])[CH:13]=[CH:12]2)C1C=CC=CC=1>CO.[Pd]>[CH3:19][CH:18]([N:14]1[C:15]2[C:11](=[CH:10][C:9]([OH:8])=[CH:17][CH:16]=2)[CH:12]=[CH:13]1)[CH2:20][CH2:21][CH3:22]

Participants

4

Reactant 1

HCID 86686447HCID 86686447, compound

Product 1

HCID 86686448HCID 86686448, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5-(Benzyloxy)-1-(pentan-2-yl)-1H-indole (8) (3.80 g, 12.9 mmol) was dissolved in methanol (MeOH, 30.0 mL) and 10% palladium on activated charcoal (Pd/C, 1.37 g, 0.129 mmol, 10 mol % Pd) was added. The mixture was placed under an atmosphere of hydrogen (double balloon), stirred overnight at room temperature, and then filtered over Celite® (MeOH eluent, 500 mL). Evaporation of the solvent under reduced pressure afforded 1-(pentan-2-yl)-1H-indol-5-ol (9) (2.60 g, 100%) as an oil. 1H NMR (500 MHz, CDCl3): δ 7.25 (d, J=9.0, 1H), 7.18 (d, J=3.0 Hz, 1H), 7.05 (d, J=2.0 Hz, 1H), 6.80 (dd, J=9.0, 2.0, 1H), 6.41 (d, J=3.0 Hz, 1H), 4.56 (bs, 1H), 4.43 (m, 1H), 1.87 (m, 2H), 1.52 (d, J=6.5, 3H), 1.26 (m, 2H), 0.90 (t, J=7.5, 3H).

Workup

  1. filtrationfiltered over Celite® (MeOH eluent, 500 mL)
  2. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-60b2dd01e74e48e4b16ecf7fa607668d
Source dataset
uspto-grants-2015_06
Patent number
US09067886B2

Reaction notes

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