Tetrahydrofuran → 6-Amino-2-fluoro-3-{[6-(methylsulfonyl)pyridin-3-yl]oxy}phenol

HRID 1188956Notes

Reaction equation

HRID 1188956 reaction equation
C([O:8][C:9]1[C:15]([F:16])=[C:14]([O:17][C:18]2[CH:19]=[N:20][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:22][CH:23]=2)[CH:13]=[CH:12][C:10]=1[NH2:11])C1C=CC=CC=1.O1CCCC1>[Pd].CO>[NH2:11][C:10]1[C:9]([OH:8])=[C:15]([F:16])[C:14]([O:17][C:18]2[CH:19]=[N:20][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:22][CH:23]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 582369482-(Benzyloxy)-3-fluoro-4-{[6-(methylsulfonyl)pyridin-3-yl]oxy}aniline

Product 1

HCID 582370436-Amino-2-fluoro-3-{[6-(methylsulfonyl)pyridin-3-yl]oxy}phenolYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-(benzyloxy)-3-fluoro-4-{[6-(methylsulfonyl)pyridin-3-yl]oxy}aniline (5.5 g), 10% palladium on carbon (containing 50% water, 1.6 g), tetrahydrofuran (100 mL) and methanol (80 mL) was hydrogenated at room temperature for 20 h under balloon pressure. The catalyst was removed by filtration and washed with tetrahydrofuran-methanol. The combined filtrate and washings were concentrated in vacuo and the residue was dissolved in ethyl acetate. The solution was concentrated in vacuo to give the title compound (4.2 g, 100%) as a light brown amorphous solid. MS 299 (MH+).

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with tetrahydrofuran-methanol
  3. concentrationThe combined filtrate and washings were concentrated in vacuo
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-342d7aefd57e4d54ac00732475a3843a
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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