Cesium fluoride → HCID 117962557, Verbindung

HRID 877469Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 877469
[Cl:1][C:2]1[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]2[C:3]=1[C:4]1[CH2:5][CH2:6][CH2:7][C:8](=[O:16])[C:9]=1[NH:10]2.[F-].[Cs+].[C:19]([Si](C)(C)C)([F:22])([F:21])[F:20]>C1COCC1>[Cl:1][C:2]1[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]2[C:3]=1[C:4]1[CH:5]([C:19]([F:22])([F:21])[F:20])[CH2:6][CH2:7][CH:8]([OH:16])[C:9]=1[NH:10]2

Komponenten

5

Edukt 3

HCID 25953Cesium fluorideHCID 552549(Trifluoromethyl)trimethylsilaneHCID 67378017HCID 67378017, Verbindung

Produkt 1

HCID 117962557HCID 117962557, VerbindungAusbeute 100,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 5,8-dichloro-2,3,4,9-tetrahydro-1H-carbazol-1-one (0.1 g, 0.39 mmol) in anhydrous THF (8 mL) at 0° C., CsF (59 mg, 0.39 mmol) and CF3TMS (0.56 g, 3.93 mmol) were added. The reaction mixture was slowly warmed to room temperature and stirred for 18 h. After the volatiles were removed in vacuo, the residue was diluted with water and extracted with EtOAc (2×15 mL) to give the crude compound which was purified by silica gel chromatography [EtOAc-hexane (1:4) as eluant] to give the title compound (0.127 g, 16%). 1H NMR (500 MHz, DMSO-d6, δ in ppm) 11.07 (s, 1H), 7.21 (d, J=8.0 Hz, 1H), 7.06 (d, J=8.5 Hz, 1H), 6.62 (s, 1H), 3.01-3.0 (m, 2H), 2.22-2.19 (m, 1H), 1.97-1.92 (m, 3H).

Aufarbeitung

  1. customAfter the volatiles were removed in vacuo
  2. additionthe residue was diluted with water
  3. extractionextracted with EtOAc (2×15 mL)
  4. customto give the crude compound which
  5. customwas purified by silica gel chromatography [EtOAc-hexane (1:4) as eluant]

Quellen und Nachweise

ORD-Eintrag
ord-d78c424ef055410097446a464fb2d310
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987319B2

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