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

HRID 1188956Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1188956
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

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

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+).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-342d7aefd57e4d54ac00732475a3843a
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673942B2

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