HCID 59627927, compound → HCID 44193191, compound

HRID 2421258Notes

Reaction equation

HRID 2421258 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:26])[C:5]2[CH:6]=[CH:7][N:8]([C:11]3[CH:16]=[CH:15][C:14]([O:17]CC4C=CC=CC=4)=[C:13]([F:25])[CH:12]=3)[C:9]=2[CH:10]=1>C(OCC)(=O)C.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([OH:26])[C:5]2[CH:6]=[CH:7][N:8]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([F:25])[CH:12]=3)[C:9]=2[CH:10]=1

Participants

4

Reactant 1

HCID 59627927HCID 59627927, compound

Product 1

HCID 44193191HCID 44193191, compoundYield 75.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6-fluoro-1-{3-fluoro-4-[(phenylmethyl)oxy]phenyl}-1H-indol-4-ol (D18) (380 mg, 1.082 mmol) in ethyl acetate (30 mL) was hydrogenated in an H-cube over a 10% palladium on charcoal catalyst. The resulting solution was concentrated. The product was purified by silica gel chromatography eluting with 10-100% ethyl acetate in hexane to yield the title compound (E9), (213 mg).

Workup

  1. concentrationThe resulting solution was concentrated
  2. customThe product was purified by silica gel chromatography
  3. washeluting with 10-100% ethyl acetate in hexane

Sources & evidence

ORD record
ord-3713f564d75d4745b329dfd4b74d6405
Source dataset
uspto-grants-2011_06
Patent number
US07956083B2

Reaction notes

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