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N-Bromosuccinamide → N-(5'-bromo-5-fluoro-3,4'-bipyridin-2'-yl)-N'-ethylurea

HRID 2243057
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2243057
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[CH:12]=[C:11]([C:13]2[CH:14]=[N:15][CH:16]=[C:17]([F:19])[CH:18]=2)[CH:10]=[CH:9][N:8]=1)=[O:5])[CH3:2].[Br:20]NC(=O)CCC(N)=O>CN(C=O)C>[Br:20][C:10]1[C:11]([C:13]2[CH:14]=[N:15][CH:16]=[C:17]([F:19])[CH:18]=2)=[CH:12][C:7]([NH:6][C:4]([NH:3][CH2:1][CH3:2])=[O:5])=[N:8][CH:9]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 9834204N-BromosuccinamideHCID 59208495HCID 59208495, Verbindung2×

Produkt 1

HCID 59208332N-(5'-bromo-5-fluoro-3,4'-bipyridin-2'-yl)-N'-ethylureaAusbeute 67,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of N-ethyl-N′-(5-fluoro-3,4′-bipyridin-2′-yl)urea (Intermediate 29, 386 mg, 1.48 mmol) in DMF (7 mL), N-bromosuccinamide (396 mg, 2.22 mmol) was added. The resulting solution was heated to 80° C. and stirred at that temperature for 8 hours. The reaction mixture was partitioned between water and ethyl acetate. The layers were separated and the organic layer was washed with 5% sodium thiosulfate solution, water and brine. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The resulting solid was washed with acetonitrile and dried to give the title compound as an off-white solid (340 mg). MS (ESP): 340 (M+H+) for C13H12BrFN4O; NMR: 1.06 (t, 3H), 3.14 (q, 2H), 7.35 (t, 1H), 7.69 (s, 1H), 7.91-7.97 (m, 1H), 8.48 (s, 1H), 8.51 (t, 1H), 8.71 (d, 1H), 9.37 (s, 1H).

Aufarbeitung

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. customThe layers were separated
  3. washthe organic layer was washed with 5% sodium thiosulfate solution, water and brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washThe resulting solid was washed with acetonitrile
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-39270512dd7c43f6a7720ca219ecc672
Quelldatensatz
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07674801B2

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