HCID 90426656, compound → HCID 90427659, compound

HRID 2279041Notes

Reaction equation

HRID 2279041 reaction equation
[Br:1][C:2]1[CH:15]=[C:14]([N+:16]([O-])=O)[C:13]([F:19])=[CH:12][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([Cl:11])[CH:6]=1>CCO.[Ni]>[Br:1][C:2]1[C:3]([O:4][C:5]2[CH:10]=[CH:9][N:8]=[C:7]([Cl:11])[CH:6]=2)=[CH:12][C:13]([F:19])=[C:14]([CH:15]=1)[NH2:16]

Participants

4

Reactant 1

HCID 90426656HCID 90426656, compound

Product 1

HCID 90427659HCID 90427659, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-(2-bromo-5-fluoro-4-nitrophenoxy)-2-chloropyridine (1.16 g, 3.34 mmol) and Raney Ni (0.5 g) in EtOH (40 mL) was hydrogenated (1 atm) overnight, the solids removed via filtration and washed with EtOH. The filtrate was concentrated to dryness, the residue dissolved in EtOAc, washed with brine, dried over Na2SO4 and concentrated to dryness to afford 5-bromo-4-((2-chloropyridin-4-yl)oxy)-2-fluoroaniline (994 mg, 94%). MS (ESI) m/z: (M+H+): 318.9.

Workup

  1. custom(1 atm) overnight
  2. customthe solids removed via filtration
  3. washwashed with EtOH
  4. concentrationThe filtrate was concentrated to dryness
  5. dissolutionthe residue dissolved in EtOAc
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-85842cae00b946c8904f0e1cda08068b
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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