HCID 59627924, compound → HCID 44193282, compound

HRID 2421259Notes

Reaction equation

HRID 2421259 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:25])[C:5]2[CH:6]=[CH:7][N:8]([C:11]3[CH:16]=[CH:15][C:14]([O:17]CC4C=CC=CC=4)=[CH:13][CH:12]=3)[C:9]=2[CH:10]=1>[Pd].C(O)C>[F:1][C:2]1[CH:3]=[C:4]([OH:25])[C:5]2[CH:6]=[CH:7][N:8]([C:11]3[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=3)[C:9]=2[CH:10]=1

Participants

4

Reactant 1

HCID 59627924HCID 59627924, compound

Product 1

HCID 44193282HCID 44193282, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 6-fluoro-1-{4-[(phenylmethyl)oxy]phenyl}-1H-indol-4-ol (D20) (75 mg) and palladium on charcoal (75 mg) in ethanol (3 mL) was stirred under hydrogen at room temperature for 3 hours. The mixture was filtered and the filtrate was evaporated and chromatographed on silica gel (0-50% ethyl acetate in hexane). The product containing fractions were concentrated and then re-evaporated from ether (3×) to give the title compound (E10) as a white solid, (15 mg).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated
  3. customchromatographed on silica gel (0-50% ethyl acetate in hexane)
  4. additionThe product containing fractions
  5. concentrationwere concentrated
  6. customre-evaporated from ether (3×)

Sources & evidence

ORD record
ord-a948f22f5170424a93423d7d51c82a4e
Source dataset
uspto-grants-2011_06
Patent number
US07956083B2

Reaction notes

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