HCID 68157886, compound → HCID 68186358, compound

HRID 243263Notes

Reaction equation

HRID 243263 reaction equation
[CH2:1]([NH:3][C:4]1[C:9]([N+:10]([O-])=O)=[CH:8][CH:7]=[C:6]([F:13])[C:5]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)[CH3:2]>[Pd].C(OCC)(=O)C>[CH2:1]([NH:3][C:4]1[C:9]([NH2:10])=[CH:8][CH:7]=[C:6]([F:13])[C:5]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)[CH3:2]

Participants

4

Reactant 1

HCID 68157886HCID 68157886, compound

Product 1

HCID 68186358HCID 68186358, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of ethyl-(3-fluoro-6-nitro-2-pyridin-2-yl-phenyl)amine (1.00 g, 3.82 mmol) and 10% palladium on carbon (0.10 g) in ethyl acetate (15 mL) was stirred under an atmosphere of hydrogen at atmospheric pressure and 20° C. for 3 days. The catalyst was removed by filtration and the resultant solution was concentrated in vacuo. The residue was purified by silica gel chromatography eluting (Si—PPC, gradient 0-100% EtOAc/cyclohexane) to give the title compound as yellow oil (0.61 g, 69%). 1H NMR (CDCl3) δ: 8.71 (1H, ddd, J=6.6, 2.5, 1.3 Hz), 7.78 (1H, ddd, J=10.5, 10.1, 2.5 Hz), 7.58 (1H, ddt, J=10.6, 5.0, 1.4 Hz), 7.27 (1H, ddd, J=10.0, 6.5, 1.6 Hz), 6.76-6.66 (2H, m), 5.24 (1H, br s), 3.82 (2H, br s), 2.76 (2H, t, J=9.5 Hz), 0.82 (3H, t, J=9.5 Hz)

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe resultant solution was concentrated in vacuo
  3. customThe residue was purified by silica gel chromatography
  4. washeluting (Si—PPC, gradient 0-100% EtOAc/cyclohexane)

Sources & evidence

ORD record
ord-b85935d19acd4e8c8b681b7142599513
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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