1-{3,5-Difluoro-4-[(phenylmethyl)oxy]phenyl}-4-hydroxy-1H-indazole-6-carbonitrile → 1-(3,5-Difluoro-4-hydroxyphenyl)-4-hydroxy-1H-indazole-6-carbonitrile

HRID 2423113Notes

Reaction equation

HRID 2423113 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:17]2[C:25]3[C:20](=[C:21]([OH:28])[CH:22]=[C:23]([C:26]#[N:27])[CH:24]=3)[CH:19]=[N:18]2)[CH:5]=[C:6]([F:16])[C:7]=1[O:8]CC1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([N:17]2[C:25]3[C:20](=[C:21]([OH:28])[CH:22]=[C:23]([C:26]#[N:27])[CH:24]=3)[CH:19]=[N:18]2)[CH:5]=[C:6]([F:16])[C:7]=1[OH:8]

Participants

4

Reactant 1

HCID 1363814391-{3,5-Difluoro-4-[(phenylmethyl)oxy]phenyl}-4-hydroxy-1H-indazole-6-carbonitrile

Product 1

HCID 1359103821-(3,5-Difluoro-4-hydroxyphenyl)-4-hydroxy-1H-indazole-6-carbonitrileYield 50.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-{3,5-difluoro-4-[(phenylmethyl)oxy]phenyl}-4-hydroxy-1H-indazole-6-carbonitrile (D37) (610 mg, 1.617 mmol) in ethyl acetate (50 mL) was passed through the H-cube over a 10% palladium on charcoal catalyst at room temperature and pressure. The filtrate was concentrated and then triturated with dichloromethane and collected by filtration to yield the desired product (E20) (235 mg).

Workup

  1. concentrationThe filtrate was concentrated
  2. customtriturated with dichloromethane
  3. filtrationcollected by filtration

Sources & evidence

ORD record
ord-6081ca7767bd4235b16e321c7bd55ef4
Source dataset
uspto-grants-2011_06
Patent number
US07960563B2

Reaction notes

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