HCID 86686447, compound → HCID 86686448, compound

HRID 2176816Notes

Reaction equation

HRID 2176816 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, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5-(Benzyloxy)-1-(pentan-2-yl)-1H-indole (8) (10.67 g, 36.4 mmol, 1.0 equiv.) was dissolved in MeOH (90 mL), and 10% wt. Pd/C was added (3.87 g, 3.64 mmol, 0.10 equiv). The reaction mixture was placed under a hydrogen atmosphere using double balloons, and stirred for 24 h at room temperature. The mixture was filtered through a Celite® pad and washed with (800 mL). The filtrate was concentrated to afford 1-(pentan-2-yl)-1H-indol-5-ol (9) as a brown oil, which was used without any further purification in the next step. 1H NMR (500 MHz, CDCl3) δ7.23 (d, J=8.8 Hz, 1H), 7.15 (d, J=2.9 Hz, 1H), 7.03 (d, J=1.8 Hz, 1H), 6.77 (dd, J=8.7, 2.0 Hz, 1H), 6.39 (d, J=2.8 Hz, 1H), 4.52 (br, 1H), 4.42 (m, 1H), 1.87 (m, 1H), 1.76 (m, 1H), 1.49 (d, J=6.8 Hz, 3H), 1.23 (m, 2H), 0.88 (t, J=7.4 Hz, 3H).

Workup

  1. filtrationThe mixture was filtered through a Celite® pad
  2. washwashed with (800 mL)
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-080bccb6805d4bc18472f2c476ed9563
Source dataset
uspto-grants-2015_06
Patent number
US09067886B2

Reaction notes

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