Benzyl Alcohol → 3-(Benzyloxy)-7-bromo-1,5-naphthyridine

HRID 513926

Reaktionsgleichung

Reaktionsgleichung von HRID 513926
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[Br:11][C:12]1[CH:13]=[N:14][C:15]2[C:20]([CH:21]=1)=[N:19][CH:18]=[C:17](Br)[CH:16]=2>CN(C=O)C>[CH2:1]([O:8][C:17]1[CH:18]=[N:19][C:20]2[C:15]([CH:16]=1)=[N:14][CH:13]=[C:12]([Br:11])[CH:21]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 12366583,7-Dibromo-1,5-naphthyridine2×

Produkt 1

HCID 904173103-(Benzyloxy)-7-bromo-1,5-naphthyridineAusbeute 36,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of benzyl alcohol (2.25 g, 20.8 mmol) in DMF (25 mL) was added NaH (60% in mineral oil, 0.83 g, 20.8 mmol). The resulting mixture was heated to 60° C. for 10 minutes and was added to 3,7-dibromo-1,5-naphthyridine (Intermediate 3, 5.0 g, 17.4 mmol) in DMF (25.0 mL) at 100° C. The resulting mixture was stirred over night at 100° C., cooled, and concentrated under reduced pressure. Water (50 mL) was added and the aqueous layer was washed with DCM (3×50 mL). The organic layers were combined, dried over Na2SO4, filtered and concentrated under reduced pressure. Purification (FCC, SiO2, DCM/petroleum ether, 1:1) afforded the title compound as a white solid (2.0 g, 36.7%).

Aufarbeitung

  1. temperaturecooled
  2. concentrationconcentrated under reduced pressure
  3. additionWater (50 mL) was added
  4. washthe aqueous layer was washed with DCM (3×50 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customPurification (FCC, SiO2, DCM/petroleum ether, 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-344092db26ed41608b66559ff67c1940
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102674B2

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