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

HRID 2423097Notes

Reaction equation

HRID 2423097 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]=[N: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]=[N:17]2)[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

5

Reactant 1

HCID 1363814381-{3-Fluoro-4-[(phenylmethyl)oxy]phenyl}-4-hydroxy-1H-indazole-6-carbonitrile

Product 1

HCID 1359103851-(3-Fluoro-4-hydroxyphenyl)-4-hydroxy-1H-indazole-6-carbonitrileYield 42.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-{3-fluoro-4-[(phenylmethyl)oxy]phenyl}-4-hydroxy-1H-indazole-6-carbonitrile (D6) (308 mg, 0.86 mmol) in ethanol (10 mL) and ethyl acetate (10 mL) was hydrogenated in an H-cube over a 10% palladium on charcoal catalyst. The resulting solution was concentrated, dissolved in ethanol then the product purified by silica gel chromatography eluting with 10-100% ethyl acetate in hexane to yield the title compound (E3) (98 mg).

Workup

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

Sources & evidence

ORD record
ord-840a636cf34b44aa94d7a8ac07143d60
Source dataset
uspto-grants-2011_06
Patent number
US07960563B2

Reaction notes

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