Ethanol → 2-(Benzyloxy)-3-fluoro-4-{[6-(methylsulfonyl)pyridin-3-yl]oxy}aniline

HRID 1188955Notes

Reaction equation

HRID 1188955 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([F:29])=[C:11]([CH:23]=[CH:24][C:25]=1[N+:26]([O-])=O)[O:12][C:13]1[CH:14]=[CH:15][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[N:17][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Ca+2].[Cl-].C(O)C>[Fe].O>[CH2:1]([O:8][C:9]1[C:10]([F:29])=[C:11]([O:12][C:13]2[CH:18]=[N:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)[CH:23]=[CH:24][C:25]=1[NH2:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 5284359Calcium ChlorideHCID 582371085-[3-(Benzyloxy)-2-fluoro-4-nitrophenoxy]-2-(methylsulfonyl)pyridine

Product 1

HCID 582369482-(Benzyloxy)-3-fluoro-4-{[6-(methylsulfonyl)pyridin-3-yl]oxy}anilineYield 70.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

A mixture of 5-[3-(benzyloxy)-2-fluoro-4-nitrophenoxy]-2-(methylsulfonyl)pyridine (8.4 g), iron (powder, 5.5 g), calcium chloride (0.24 g), ethanol (200 mL) and water (40 mL) was refluxed for 4 h. The mixture was cooled to room temperature and filtered through a celite pad. The filtrate was concentrated in vacuo to remove ethanol. The residue was partitioned between ethyl acetate and brine. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate:hexane=20:80 to 40:60, volume ratio) to give the title compound (5.5 g, 70%) as a dark green oil. MS 389 (MH+).

Workup

  1. temperaturewas refluxed for 4 h
  2. filtrationfiltered through a celite pad
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto remove ethanol
  5. customThe residue was partitioned between ethyl acetate and brine
  6. washThe organic layer was washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by silica gel chromatography (ethyl acetate:hexane=20:80 to 40:60, volume ratio)

Sources & evidence

ORD record
ord-51e396482b914a9b98f332fae5dcef8c
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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