HCID 58459211, compound → HCID 55067727, compound

HRID 243168Notes

Reaction equation

HRID 243168 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2[N+:17]([O-])=O)[CH:5]=[C:6]([F:8])[CH:7]=1>CCOC(C)=O.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:11]([NH2:17])=[CH:12][CH:13]=[C:14]([F:16])[CH:15]=2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 1

HCID 58459211HCID 58459211, compound

Product 1

HCID 55067727HCID 55067727, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of (3,5-difluorophenyl)-(5-fluoro-2-nitrophenyl)amine (2.0 g, 7.5 mmol) in EtOAc (65 mL) was added to a slurry of palladium on carbon (10% by wt, 200 mg) in EtOAc (10 mL) under nitrogen. The reaction mixture was stirred at RT under an atmosphere of hydrogen for 4 h. The mixture was filtered through Celite® and the filtrate concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PPC, gradient 0-30% EtOAc/cyclohexane) to afford the title compound as a white solid that turned red upon standing (1.07 g, 60%). LCMS (Method C): RT 3.40 min [M+H]+ 239. 1H NMR (CDCl3, 400 MHz): δ 6.90-6.87 (1H, m), 6.81-6.73 (2H, m), 6.31-6.23 (3H, m), 5.42 (1H, bs), 3.58 (2H, bs).

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe resulting residue was purified by column chromatography (Si—PPC, gradient 0-30% EtOAc/cyclohexane)

Sources & evidence

ORD record
ord-79eba3570d39421883b4d10fe8b42d6c
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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