5-Chloro-2-(2-fluoro-6-methoxy-phenoxy)-3-nitro-pyridine → 5-Chloro-2-(2-fluoro-6-methoxy-phenoxy)-pyridin-3-ylamine

HRID 1898051Notes

Reaction equation

HRID 1898051 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:18]([O-])=O)[C:5]([O:8][C:9]2[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=2[F:17])=[N:6][CH:7]=1>CC(O)=O.CCOC(C)=O.[Fe]>[Cl:1][C:2]1[CH:3]=[C:4]([NH2:18])[C:5]([O:8][C:9]2[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=2[F:17])=[N:6][CH:7]=1

Participants

5

Reactant 1

HCID 666488545-Chloro-2-(2-fluoro-6-methoxy-phenoxy)-3-nitro-pyridine

Product 1

HCID 579422525-Chloro-2-(2-fluoro-6-methoxy-phenoxy)-pyridin-3-ylamine

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

AcOH (30 mL) and iron powder (5 g) were charged into a round bottom flask equipped with a magnetic stirring bar and warmed to 80° C. A solution of crude 5-chloro-2-(2-fluoro-6-methoxy-phenoxy)-3-nitro-pyridine in AcOH was added slowly into the mixture, keeping the temperature under 85° C. The reaction mixture was then cooled to room temperature, diluted with EtOAc, and filtered through a pad of Celite. The filtrate was concentrated under reduced pressure and the residue was partitioned between NaHCO3 and EtOAc. The organic portion was separated and the aqueous portion was extracted with EtOAc. The combined extracts were dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel to provide 5-chloro-2-(2-fluoro-6-methoxy-phenoxy)-pyridin-3-ylamine (3.56 g) as a colorless powder.

Workup

  1. customequipped with a magnetic stirring bar
  2. customunder 85° C
  3. temperatureThe reaction mixture was then cooled to room temperature
  4. filtrationfiltered through a pad of Celite
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was partitioned between NaHCO3 and EtOAc
  7. customThe organic portion was separated
  8. extractionthe aqueous portion was extracted with EtOAc
  9. dry with materialThe combined extracts were dried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-f37197df8403403da84ff7ba7ee685c6
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

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