HCID 66767077, compound → HCID 66767175, compound

HRID 1661983Notes

Reaction equation

HRID 1661983 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-b287010146fd48f7b1c056c3b8c6d40d
Source dataset
uspto-grants-2011_10
Patent number
US08030302B2

Reaction notes

Loading…