Quinoline → 5-(4-fluorophenyl)-5H,6aH-benzo[4,5][1,3]oxazino[3,2-a]quinoline

HRID 1501294

Reaktionsgleichung

Reaktionsgleichung von HRID 1501294
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[F:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=1.FC(F)(F)S(O[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[Si](C)(C)C)(=O)=O.[F-].[K+].C1OCCOCCOCCOCCOCCOC1>C1COCC1>[F:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]2[O:17][CH:2]3[CH:3]=[CH:4][C:5]4[C:10]([N:1]3[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]2=3)=[CH:9][CH:8]=[CH:7][CH:6]=4)=[CH:14][CH:13]=1

Komponenten

7

Edukt 5

HCID 7047QuinolineHCID 2855718-Crown-6HCID 680234-FluorobenzaldehydeHCID 522689Potassium FluorideHCID 33840072-(Trimethylsilyl)phenyl trifluoromethanesulfonate

Produkt 1

HCID 1185493045-(4-fluorophenyl)-5H,6aH-benzo[4,5][1,3]oxazino[3,2-a]quinolineAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Following the general procedure, treatment of quinoline (0.064 g, 59 μL, 0.50 mmol) and 4-fluorobenzaldehyde (0.093 g, 80 μL, 0.75 mmol) with 2-(trimethylsilyl)phenyl trifluoromethanesulfonate (0.179 g, 146 μL, 0.60 mmol) in the presence of KF (0.070 g, 1.2 mmol) and 18-crown-6 (0.317 g, 1.2 mmol) in THF (2.0 mL) at 10° C. to room temperature for 12 hrs followed by flash column chromatography (Pet. ether/EtOAc=75/25) of the crude reaction mixture afforded 5-(4-fluorophenyl)-5H,6aH-benzo[4,5][1,3]oxazino[3,2-a]quinoline as inseparable mixture of diastereomers as a yellow solid (0.158 g, 96% yield, dr determined by 1H NMR analysis of crude reaction mixture is >20:1).

Aufarbeitung

  1. customat 10° C. to room temperature
  2. customfor 12 hrs
  3. customreaction mixture

Quellen und Nachweise

ORD-Eintrag
ord-384a174ad1f74eab94ecaff11eebf043
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09206196B1

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