1-{3-Fluoro-4-[(phenylmethyl)oxy]phenyl}-4-hydroxy-1H-indole-6-carbonitrile → 1-(3-Fluoro-4-hydroxyphenyl)-4-hydroxy-1H-indole-6-carbonitrile

HRID 2421257Notes

Reaction equation

HRID 2421257 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:16]2[C:24]3[C:19](=[C:20]([OH:27])[CH:21]=[C:22]([C:25]#[N:26])[CH:23]=3)[CH:18]=[CH:17]2)[CH:5]=[CH:6][C:7]=1[O:8]CC1C=CC=CC=1>C(O)C.C(OCC)(=O)C.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([N:16]2[C:24]3[C:19](=[C:20]([OH:27])[CH:21]=[C:22]([C:25]#[N:26])[CH:23]=3)[CH:18]=[CH:17]2)[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

5

Reactant 1

HCID 668767931-{3-Fluoro-4-[(phenylmethyl)oxy]phenyl}-4-hydroxy-1H-indole-6-carbonitrile

Product 1

HCID 441931901-(3-Fluoro-4-hydroxyphenyl)-4-hydroxy-1H-indole-6-carbonitrileYield 73.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-{3-fluoro-4-[(phenylmethyl)oxy]phenyl}-4-hydroxy-1H-indole-6-carbonitrile (D14) (320 mg, 0.89 mmol) in ethanol (25 mL) and ethyl acetate (5 mL) was hydrogenated in an H-cube over a 10% palladium on charcoal catalyst. The resulting solution was concentrated and the product purified by silica gel chromatography eluting with 2-60% ethyl acetate in hexane to yield the title compound (E8), (175 mg).

Workup

  1. concentrationThe resulting solution was concentrated
  2. customthe product purified by silica gel chromatography
  3. washeluting with 2-60% ethyl acetate in hexane

Sources & evidence

ORD record
ord-8d62fd97c7a54094b7a7171e09df191e
Source dataset
uspto-grants-2011_06
Patent number
US07956083B2

Reaction notes

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