Tetrahydrofuran → HCID 71128758, compound

HRID 1624041Notes

Reaction equation

HRID 1624041 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]3[CH:11]=[N:12][NH:13][C:14]=3[CH2:15][CH2:16][CH:17]=2)=[CH:5][CH:4]=1.C1COCC1>CCO.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH2:17][CH2:16][CH2:15][C:14]3[NH:13][N:12]=[CH:11][C:10]2=3)=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 71114853HCID 71114853, compound

Product 1

HCID 71128758HCID 71128758, compoundYield 85.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-(4-Methoxyphenyl)-6,7-dihydro-1H-indazole (0.141 g, 0.62 mmol) is dissolved in EtOH (10 mL) and THF (4 mL) and 5% Pd/C (0.090 g) is added. The mixture is stirred under hydrogen (40 psi) for 4 hrs. The mixture is filtered through diatomaceous earth and the filtrate is evaporated to dryness. The residue is purified by silica gel chromatography eluting with 98:2 CH2Cl2:MeOH to give the title compound (0.121 g, 85%). ES/MS m/z 229 (M+1).

Workup

  1. filtrationThe mixture is filtered through diatomaceous earth
  2. customthe filtrate is evaporated to dryness
  3. customThe residue is purified by silica gel chromatography
  4. washeluting with 98:2 CH2Cl2

Sources & evidence

ORD record
ord-bafa32eafbed4ce68ca184ad844435c0
Source dataset
uspto-grants-2014_07
Patent number
US08778984B2

Reaction notes

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