1-(3-(Benzyloxy)-2-fluoro-6-nitrophenyl)propan-2-one → 4-fluoro-2-methyl-1H-indol-5-ol

HRID 2222406Notes

Reaction equation

HRID 2222406 reaction equation
[C:1]([CH2:4][C:5]1[C:6]([F:22])=[C:7]([O:14]CC2C=CC=CC=2)[CH:8]=[CH:9][C:10]=1[N+:11]([O-])=O)(=O)[CH3:2]>C(O)C.C(O)(=O)C.[Pd]>[F:22][C:6]1[C:7]([OH:14])=[CH:8][CH:9]=[C:10]2[C:5]=1[CH:4]=[C:1]([CH3:2])[NH:11]2

Participants

5

Reactant 1

HCID 112896631-(3-(Benzyloxy)-2-fluoro-6-nitrophenyl)propan-2-one

Product 1

HCID 103520364-fluoro-2-methyl-1H-indol-5-ol

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A solution of 3-acetylmethyl-1-benzyloxy-2-fluoro-4-nitrobenzene (300 mg, 0.99 mmol) in ethanol (10 ml) and acetic acid (1 ml) containing 10% palladium on charcoal (30 mg) was hydrogenated at 2 atmospheres pressure for 2 hours. The mixture was filtered and the filtrate was evaporated. The residue was dissolved in ethyl acetate and the organic layer was washed with aqueous sodium hydrogen carbonate, brine and evaporated to give 4-fluoro-5-hydroxy-2-methylindole. The residue was purified by column chromatography eluting with ethyl acetate/petroleum ether (3/7) to give 4-fluoro-5-hydroxy-2-methylindole (63 mg, 30%). Analytical data as above.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washthe organic layer was washed with aqueous sodium hydrogen carbonate, brine
  5. customevaporated

Sources & evidence

ORD record
ord-d88df314f86241d0a78be4581e3ca3b9
Source dataset
uspto-grants-2008_05
Patent number
US07371765B2

Reaction notes

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