5-Benzyloxy-1-(4-fluoro-phenyl)-1H-indole → 1-(4-Fluoro-phenyl)-2,3-dihydro-1H-indol-5-ol

HRID 1633670Notes

Reaction equation

HRID 1633670 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)[CH:13]=[CH:12]2)C1C=CC=CC=1>C(O)(=O)C.[Pd]>[F:24][C:21]1[CH:22]=[CH:23][C:18]([N:14]2[C:15]3[C:11](=[CH:10][C:9]([OH:8])=[CH:17][CH:16]=3)[CH2:12][CH2:13]2)=[CH:19][CH:20]=1

Participants

4

Reactant 1

HCID 111979085-Benzyloxy-1-(4-fluoro-phenyl)-1H-indole

Product 1

HCID 186794221-(4-Fluoro-phenyl)-2,3-dihydro-1H-indol-5-olYield 44%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

3.17 g (10 mmol) 5-Benzyloxy-1-(4-fluoro-phenyl)-1H-indole in 25 ml acetic acid was hydrogenated in the presence of 300 mg 10%Pd/C, filtered and hydrogenated with 60 mg PtO2 for 3 h. The catalyst was removed by filtration and the solution concentrated. The residue was dissolved in 15 ml trifluoroacetic acid and treated with 1.9 g (30 mml) sodium cyanoborhydride at 0° C. The solution was stirred at RT for 30 min, concentrated and dissolved in ether, 0.5M NaOH. The inorganic phase was extracted with ether, the combined organic phases were washed with brine and dried over Na2SO4. Column chromatography on silica gel with CH2Cl2/MeOH 19:1 yielded 1.0 g (44%) 1-(4-Fluoro-phenyl)-2,3-dihydro-1H-indol-5-ol as colorless solid; MS: 229 (M).

Workup

  1. filtrationfiltered
  2. customThe catalyst was removed by filtration
  3. concentrationthe solution concentrated
  4. dissolutionThe residue was dissolved in 15 ml trifluoroacetic acid
  5. additiontreated with 1.9 g (30 mml) sodium cyanoborhydride at 0° C
  6. concentrationconcentrated
  7. dissolutiondissolved in ether
  8. extractionThe inorganic phase was extracted with ether
  9. washthe combined organic phases were washed with brine
  10. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-18a2d8871075470da94ffb4166044597
Source dataset
uspto-grants-2003_01
Patent number
US06503907B2

Reaction notes

Loading…