HCID 59627925, compound → HCID 44193285, compound

HRID 2421262Notes

Reaction equation

HRID 2421262 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([O:9]CC2C=CC=CC=2)[CH:5]=[CH:4][C:3]=1[N:17]1[C:25]2[C:20](=[C:21]([O:26]CC3C=CC=CC=3)[CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18]1>C(OCC)(=O)C.[Pd]>[F:1][C:2]1[C:7]([F:8])=[C:6]([OH:9])[CH:5]=[CH:4][C:3]=1[N:17]1[C:25]2[CH:24]=[CH:23][CH:22]=[C:21]([OH:26])[C:20]=2[CH:19]=[CH:18]1

Participants

4

Reactant 1

HCID 59627925HCID 59627925, compound

Product 1

HCID 44193285HCID 44193285, compoundYield 53.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1-{2,3-difluoro-4-[(phenylmethyl)oxy]phenyl}-4-[(phenylmethyl)oxy]-1H-indole (D23) (141 mg, 0.319 mmoL) was dissolved in ethyl acetate (10 mL) and was hydrogenated at room temperature and atmospheric pressure in the presence of 10% palladium on charcoal (50% wet) (70 mg). After 22 hours the mixture was filtered and concentrated in vacuo. The crude product was purified by MDAP and the isolated material was partitioned between ethyl acetate and sat. NH4Cl. The phases were separated and the aqueous phase extracted with more ethyl acetate. The combined organic phases were washed with brine, dried over MgSO4, filtered and concentrated to afford the title compound (E13), (45 mg).

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationAfter 22 hours the mixture was filtered
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by MDAP
  5. customthe isolated material was partitioned between ethyl acetate and sat. NH4Cl
  6. customThe phases were separated
  7. extractionthe aqueous phase extracted with more ethyl acetate
  8. washThe combined organic phases were washed with brine
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-0caa00ba3a5e4c618981625c0e1de768
Source dataset
uspto-grants-2011_06
Patent number
US07956083B2

Reaction notes

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