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

HRID 930934Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 930934
[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 311a (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 (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 (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by chromatography (silica gel, 0-50% ethyl acetate in heptanes)

Quellen und Nachweise

ORD-Eintrag
ord-e9d620f55da54434a8eef52e24f05f50
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296741B2

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