4-allyl-5-hydroxy-N-(4-fluorobenzyl)indole → 4-propyl-5-hydroxy-N-(4-fluorobenzyl)indole

HRID 342774Notes

Reaction equation

HRID 342774 reaction equation
[CH2:1]([C:4]1[C:12]([OH:13])=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)[CH:2]=[CH2:3]>C(OCC)(=O)C.[Pd]>[CH2:1]([C:4]1[C:12]([OH:13])=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[CH2:14][C:15]1[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=1)[CH2:2][CH3:3]

Participants

4

Reactant 1

HCID 539788064-allyl-5-hydroxy-N-(4-fluorobenzyl)indole

Product 1

HCID 537011994-propyl-5-hydroxy-N-(4-fluorobenzyl)indole

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4-allyl-5-hydroxy-N-(4-fluorobenzyl)indole (Step C; 0.40 g, 1.42 mmol) was taken up in 10 mL ethyl acetate and hydrogenated (1 atm) at ambient temperature using 5% palladium on charcoal (15 mg) for 2 hours. The reaction was filtered through celite and concentrated in vacuo to provide the title compound which was used without further purification.

Workup

  1. customat ambient temperature
  2. customfor 2 hours
  3. filtrationThe reaction was filtered through celite and
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9aff132308f947809bee9000b430f7ab
Source dataset
uspto-grants-1999_01
Patent number
US05859051

Reaction notes

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