Potassium Acetate → 2-Bromo-4-fluoro-6-(1-oxo-6,7,8,9-tetrahydropyrazino[1,2-a]indol-2(1H)-yl)benzaldehyde

HRID 1026487

Reaktionsgleichung

Reaktionsgleichung von HRID 1026487
[C:1]1(=[O:14])[C:6]2=[CH:7][C:8]3[CH2:9][CH2:10][CH2:11][CH2:12][C:13]=3[N:5]2[CH:4]=[CH:3][NH:2]1.[Br:15][C:16]1[CH:23]=[C:22]([F:24])[CH:21]=[C:20](Br)[C:17]=1[CH:18]=[O:19].C([O-])(=O)C.[K+].COC1C2C(=C3C(=CC=2)C(OC)=CC=N3)N=CC=1>>[Br:15][C:16]1[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([N:2]2[CH:3]=[CH:4][N:5]3[C:13]4[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=4[CH:7]=[C:6]3[C:1]2=[O:14])[C:17]=1[CH:18]=[O:19]

Komponenten

5

Edukt 4

HCID 517044Potassium AcetateHCID 104622984,7-Dimethoxy-1,10-phenanthrolineHCID 444746662,6-Dibromo-4-fluorobenzaldehydeHCID 866837556,7,8,9-Tetrahydropyrazino[1,2-a]indol-1(2H)-one

Produkt 1

HCID 866837562-Bromo-4-fluoro-6-(1-oxo-6,7,8,9-tetrahydropyrazino[1,2-a]indol-2(1H)-yl)benzaldehydeAusbeute 49,3 %

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 121e (500 mg, 2.66 mmol), 2,6-dibromo-4-fluorobenzaldehyde (1.50 g, 5.32 mmol), and potassium acetate (521 mg, 5.32 mmol). After bubbling argon through the suspension for 30 minutes, 4,7-dimethoxy-1,10-phenanthroline (638.4 mg, 2.66 mmol) and cuprous iodide (506 mg, 2.66 mmol) were added. The system was subjected to three cycles of vacuum/argon flush and then heated at 100° C. for 16 h. It was then cooled to room temperature and filtered. The solid was washed with dichloromethane (2×100 ml). The combined filtrate was concentrated under reduced pressure and the residue was purified by silica-gel column chromatography eluting with petroleum ether/ethyl acetate (10:1 to 3:1) to afford 121f (510 mg, 49%) as a yellow solid. MS: [M+H]+ 389.

Aufarbeitung

  1. customA 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser
  2. customAfter bubbling argon through the suspension for 30 minutes
  3. customflush
  4. temperatureIt was then cooled to room temperature
  5. filtrationfiltered
  6. washThe solid was washed with dichloromethane (2×100 ml)
  7. concentrationThe combined filtrate was concentrated under reduced pressure
  8. customthe residue was purified by silica-gel column chromatography
  9. washeluting with petroleum ether/ethyl acetate (10:1 to 3:1)

Quellen und Nachweise

ORD-Eintrag
ord-6c67023df6bd4e6a876cecd42924a331
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08729072B2

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