Sodium hydride → HCID 86679725, Verbindung

HRID 77440Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 77440
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]=[CH:5]2.[H-].[Na+].[CH3:15][Si:16]([CH2:19][CH2:20][O:21][CH2:22]Cl)([CH3:18])[CH3:17]>CN(C=O)C.[Cl-].[NH4+]>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[N:8]([CH2:22][O:21][CH2:20][CH2:19][Si:16]([CH3:18])([CH3:17])[CH3:15])[C:7](=[O:12])[CH:6]=[CH:5]2

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 125201446-Bromo-1,8-naphthyridin-2(1H)-one

Produkt 1

HCID 86679725HCID 86679725, VerbindungAusbeute 76,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 6-bromo-1,8-naphthyridin-2(1H)-one (0.1 g, 0.444 mmol) in DMF (2 mL) was added sodium hydride (0.021 g, 0.889 mmol) at 0° C. The reaction was stirred at 0° C. for 30 min, then SEM-Cl (0.118 mL, 0.667 mmol) was added. The reaction was stirred at room temperature overnight, then diluted with ammonium chloride solution, extracted with ethyl acetate, dried over Na2SO4, and concentrated. The crude product was purified by flash chromatography on silica gel using 20% ethyl acetate in petroleum ether to give 6-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1,8-naphthyridin-2(1H)-one (0.12 g, 76%). 1HNMR 400 MHz (CDCl3): 0.034 (s, 9H), 0.95-0.99 (m, 2H), 3.73-3.77 (m, 2H), 5.92 (s, 2H), 6.75-6.77 (m, 1H), 7.56-7.58 (m, 1H), 7.96-7.98 (m, 1H), 8.63-8.64 (m, 1H).

Aufarbeitung

  1. stirringThe reaction was stirred at room temperature overnight
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography on silica gel using 20% ethyl acetate in petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-ffd31b84476e4888adadf7a90b84ac49
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841301B2

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