Methanol → (5-Bromo-6-(2,4-difluorophenoxy)pyridin-3-yl)methanol

HRID 633555Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 633555
[Br:1][C:2]1[C:3]([O:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[F:19])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7](O)=[O:8].CO>O1CCCC1>[Br:1][C:2]1[CH:10]=[C:6]([CH2:7][OH:8])[CH:5]=[N:4][C:3]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[F:19]

Komponenten

4

Edukt 2

HCID 887MethanolHCID 867210745-Bromo-6-(2,4-difluorophenoxy)nicotinic acid

Produkt 1

HCID 86721075(5-Bromo-6-(2,4-difluorophenoxy)pyridin-3-yl)methanolAusbeute 76,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

The product from Example 60A (1.0 g, 3.03 mmol) and borane tetrahydrofuran complex (6.06 mL, 6.06 mmol) were combined in tetrahydrofuran (15.15 mL) and heated at 50° C. for 2 hours, cooled, treated with 10 mL of methanol, heated at 50° C. for 1 hour, cooled and concentrated. The residue was partitioned between ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride, dried (anhydrous Na2SO4), filtered, and concentrated. Purification by chromatography (silica gel, 0-50% ethyl acetate in heptanes) afforded the title compound (0.73 g, 76%).

Aufarbeitung

  1. temperaturecooled
  2. temperatureheated at 50° C. for 1 hour
  3. temperaturecooled
  4. concentrationconcentrated
  5. customThe residue was partitioned between ethyl acetate and water
  6. washThe organic layer was washed with saturated aqueous sodium chloride
  7. dry with materialdried (anhydrous Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by chromatography (silica gel, 0-50% ethyl acetate in heptanes)

Quellen und Nachweise

ORD-Eintrag
ord-fde6517d98a84c2b88043aa5f380f0a8
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321764B2

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