HCID 66767077, compound → HCID 66767175, compound

HRID 2195499Notes

Reaction equation

HRID 2195499 reaction equation
[F:1][C:2]1[CH:33]=[C:32]([N+:34]([O-])=O)[CH:31]=[CH:30][C:3]=1[O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[C:14]1[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=1)[N:10]([CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][O:25]1)[N:9]=[CH:8]2>CCOC(C)=O.[Pd]>[F:1][C:2]1[CH:33]=[C:32]([CH:31]=[CH:30][C:3]=1[O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[C:14]1[CH:15]=[CH:16][C:17]([S:20]([CH3:23])(=[O:21])=[O:22])=[CH:18][CH:19]=1)[N:10]([CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][O:25]1)[N:9]=[CH:8]2)[NH2:34]

Participants

4

Reactant 1

HCID 66767077HCID 66767077, compound

Product 1

HCID 66767175HCID 66767175, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-(2-fluoro-4-nitrophenoxy)-6-(4-(methylsulfonyl)phenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (320 mg, 0.63 mmol) in EtOAc (50 mL) is added Pd/C (10%, 100 mg). The resulting mixture is degassed by evacuation and backfilled with H2 three times. It is stirred under an atmosphere of H2 at RT overnight. The solid is removed by filtration and the filtrate is concentrated. The residue is purified by silica gel column chromatography eluting with DCM:MeOH (20:1) to give the desired product (250 mg, 83% yield). MS (m/z): 482.1 (M+H).

Workup

  1. customThe resulting mixture is degassed by evacuation
  2. customThe solid is removed by filtration
  3. concentrationthe filtrate is concentrated
  4. customThe residue is purified by silica gel column chromatography
  5. washeluting with DCM:MeOH (20:1)

Sources & evidence

ORD record
ord-82142e6d7d474e369c0cbbc8d17883e7
Source dataset
uspto-grants-2012_12
Patent number
USRE043878E1

Reaction notes

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