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

HRID 1501295

Reaktionsgleichung

Reaktionsgleichung von HRID 1501295
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Br:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH:15]=[O:16].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>[Br:11][C:12]1[CH:13]=[C:14]([CH:15]2[O:16][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:17]=[CH:18][CH:19]=1

Komponenten

7

Edukt 5

HCID 7047QuinolineHCID 2855718-Crown-6HCID 765833-BromobenzaldehydeHCID 522689Potassium FluorideHCID 33840072-(Trimethylsilyl)phenyl trifluoromethanesulfonate

Produkt 1

HCID 1185493105-(3-bromophenyl)-5H,6aH-benzo[4,5][1,3]oxazino[3,2-a]quinolineAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Following the general procedure, treatment of quinoline (0.064 g, 59 μL, 0.50 mmol) and 3-bromobenzaldehyde (0.139 g, 88 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-(3-bromophenyl)-5H,6aH-benzo[4,5][1,3]oxazino[3,2-a]quinoline as a yellow solid (0.127 g, 65% 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-cea248ff3e7b449a9740fcfa510e8842
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09206196B1

Verknüpfte Notizen

Wird geladen…