Benzyl Bromide → HCID 86723586, Verbindung

HRID 918914Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 918914
[Br:1][C:2]1[C:3]2[CH:4]=[CH:5][CH:6]=[N:7][C:8]=2[C:9](=[O:12])[NH:10][CH:11]=1.[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH2:13]([N:10]1[C:9](=[O:12])[C:8]2[N:7]=[CH:6][CH:5]=[CH:4][C:3]=2[C:2]([Br:1])=[CH:11]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 124414145-Bromo-1,7-naphthyridin-8(7H)-one

Produkt 1

HCID 86723586HCID 86723586, VerbindungAusbeute 83,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a suspension of 5-bromo-1,7-naphthyridin-8(7H)-one (0.50 g, 2.22 mmol) in anhydrous DMF (60 mL) was added benzyl bromide (0.34 mL, 2.88 mmol) and Cs2CO3 (0.94 g, 2.88 mmol). The reaction was stirred at rt for 16 h. After that time the reaction was concentrated under reduced pressure, diluted with water (50 mL) and extracted with ethyl acetate (100 mL). The organic phase was washed with water then brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The product was purified by flash column chromatography (silica gel, 98:2 dichloromethane/methanol) to give 7-benzyl-5-bromo-1,7-naphthyridin-8(7H)-one (0.584 g, 83%) as a brown solid: 1H NMR (400 MHz, CDCl3) δ 8.93 (dd, J=4.4, 1.5 Hz, 1H), 8.16 (dd, J=8.2, 1.5 Hz, 1H), 7.66 (dd, J=8.2, 4.4 Hz, 1H), 7.42 (s, 1H), 7.28-7.41 (m, 5H), 5.28 (s, 2H); ESI MS m/z 314.9 [M+H]+ and 316.9 [M+H]+.

Aufarbeitung

  1. concentrationAfter that time the reaction was concentrated under reduced pressure
  2. additiondiluted with water (50 mL)
  3. extractionextracted with ethyl acetate (100 mL)
  4. washThe organic phase was washed with water
  5. dry with materialbrine, dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe product was purified by flash column chromatography (silica gel, 98:2 dichloromethane/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-4870bd8bb5c141bea6d6fbd800b39a4b
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09271978B2

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