2-Pyrrolidone → 1-(2-(6-Bromopyridin-3-yl)ethyl)pyrrolidin-2-one

HRID 1400905Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1400905
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9]Br)=[CH:4][N:3]=1.[NH:11]1[CH2:15][CH2:14][CH2:13][C:12]1=[O:16].[H-].[Na+]>CO.C(OCC)(=O)C>[Br:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][CH2:9][N:11]2[CH2:15][CH2:14][CH2:13][C:12]2=[O:16])=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 120252-PyrrolidoneHCID 24758Sodium hydrideHCID 584744292-Bromo-5-(2-bromoethyl)pyridine

Produkt 1

HCID 584748611-(2-(6-Bromopyridin-3-yl)ethyl)pyrrolidin-2-oneAusbeute 75,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21584119Ethylacetate methanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a mixture of dibromide 290 (1.7 g, 6.4 mmol) in 2-pyrrolidone (10 mL, 130 mmol) at room temperature was added sodium hydride, 40% dispersion in mineral oil (1.16 g, 19.3 mmol). This reaction mixture was then heated to 100° C. for 2 h, then cooled to RT and partitioned between water and ethyl acetate. The organic phase was collected, washed with water, saturated aqueous ammonium chloride, and brine. It was then dried (anhydrous MgSO4), filtered and concentrated. Silica gel chromatography (10% methanol/ethyl acetate) gave title compound 291 (1.3 g, 75% yield) as a colorless solid. 1H NMR (400 MHz, CDCl3) δ (ppm): 8.17-8.16 (m, 1H); 7.42-7.37 (m, 2H); 3.49 (t, J=7.4, 2H); 3.28 (t, J=6.9, 2H); 2.79 (t, J=7.2, 2H); 2.30 (t, J=7.8, 2H); 1.95 (quintet, 7.6, 2H). MS (M+H): 269.1, 271.1

Aufarbeitung

  1. temperaturecooled to RT
  2. custompartitioned between water and ethyl acetate
  3. customThe organic phase was collected
  4. washwashed with water, saturated aqueous ammonium chloride, and brine
  5. dry with materialIt was then dried (anhydrous MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-eef4bc2510da43359eb3101a2a17614f
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08906852B2

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