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Azobisisobutyronitrile → 7-bromo-5-(2-chloro-4-fluorophenyl)-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one

HRID 394180
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Reaktionsgleichung

Reaktionsgleichung von HRID 394180
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:20])[N:9]2[C:12]2[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:19])=[C:4]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=2[Cl:28])[N:3]=1.BrN1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.N12CCCN=C1CCCCC2>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:20])[N:9]2[C:12]2[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:19])=[C:4]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=2[Cl:28])[N:3]=1
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Komponenten

6

Edukt 4

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 226480887-bromo-5-(2-chloro-4-fluorophenyl)-1-(2,6-dichlorophenyl)-3,4-dihydro-1,6-naphthyridin-2(1H)-one

Produkt 1

HCID 226479107-bromo-5-(2-chloro-4-fluorophenyl)-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

To 7-bromo-5-(2-chloro-4-fluorophenyl)-1-(2,6-dichlorophenyl)-3,4-dihydro-1,6-naphthyridin-2(1H)-one (2.33 g, 4.65 mmol) in 75 mL of CCl4 was added recrystallized N-bromosuccinimide (993 mg, 5.58 mmol) and 2,2′azobis(2-methylpropionitrile) (76.4 mg, 0.465 mmol). The resulting reaction mixture was evacuated and flushed with argon 3 times, then heated and maintained at reflux for 2.5 h. 1,8-diazabicyclo[5.4.0]undec-7-ene (695 μL, 4.65 mmol) was added and the reaction mixture was cooled to rt, washed with 140 mL of half-saturated aqueous NaHCO3, and the aqueous layer was back-extracted with 2×70 mL of ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The product was purified by flash chromatography on Biotage 40M column, eluting with a gradient system of 90:10 hexanes-ethyl acetate to 80:20 hexanes-ethyl acetate to yield 7-bromo-5-(2-chloro-4-fluorophenyl)-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one as an off white solid. Mass spectrum (ESI) 497 (M+1). 1H NMR (500 MHz, CDCl3): δ 6.64 (s, 1H); 6.79 (d, J=10.1 Hz, 1H); 7.21 (m, 1H), 7.31 (m, 1H); 7.54 (m, 3H); 7.65 (m, 2H),

Aufarbeitung

  1. customThe resulting reaction mixture
  2. customwas evacuated
  3. customflushed with argon 3 times
  4. temperatureheated
  5. temperaturemaintained
  6. temperatureat reflux for 2.5 h
  7. washwashed with 140 mL of half-saturated aqueous NaHCO3
  8. extractionthe aqueous layer was back-extracted with 2×70 mL of ethyl acetate
  9. washThe combined organic layers were washed with brine
  10. dry with materialdried over Na2SO4
  11. concentrationconcentrated under reduced pressure
  12. customThe product was purified by flash chromatography on Biotage 40M column
  13. washeluting with a gradient system of 90:10 hexanes-ethyl acetate to 80:20 hexanes-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-8dfab15aa05a4959b71f39e9d75e9120
Quelldatensatz
uspto-grants-2004_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06809199B2

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