Cesium carbonate → 6-bromo-1-cyclobutyl-5-fluoro-1H-indole-3-carbonitrile

HRID 1028006Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1028006
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]#[N:12])=[CH:7][NH:8]2)=[CH:4][C:3]=1[F:13].C(=O)([O-])[O-].[Cs+].[Cs+].[CH:20]1(Br)[CH2:23][CH2:22][CH2:21]1>CN(C=O)C>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]#[N:12])=[CH:7][N:8]2[CH:20]2[CH2:23][CH2:22][CH2:21]2)=[CH:4][C:3]=1[F:13]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 78110BromocyclobutaneHCID 534029576-Bromo-5-fluoro-1H-indole-3-carbonitrile

Produkt 1

HCID 667306106-bromo-1-cyclobutyl-5-fluoro-1H-indole-3-carbonitrileAusbeute 91,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To 6-bromo-5-fluoro-1H-indole-3-carbonitrile (49.2 g, 206 mmol) [prepared as in Example 6, Step B] was added cesium carbonate (133 g, 408 mmol), DMF (200 mL), and cyclobutylbromide (30 mL, 311 mmol). This mixture was stirred at 90° C. for three days, cooled to room temperature and poured into ice water. The precipitate was collected, washed with water and dried to give 6-bromo-1-cyclobutyl-5-fluoro-1H-indole-3-carbonitrile as a light grey solid (55 g, 90%).

Aufarbeitung

  1. temperaturecooled to room temperature
  2. customThe precipitate was collected
  3. washwashed with water
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-74bf8fa4c0214434bc5379f59f77134b
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08735414B2

Notizen zur Reaktion

Wird geladen…