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Potassium Carbonate → 2-Phenyl-3-p-tolyl-pyrido[2,3-b]pyrazine

HRID 2276597
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2276597
Cl[C:2]1[N:3]=[C:4]2[CH:18]=[CH:17][CH:16]=[N:15][C:5]2=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1.[C:19]1(B(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:19]1([C:2]2[N:3]=[C:4]3[CH:18]=[CH:17][CH:16]=[N:15][C:5]3=[N:6][C:7]=2[C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 866818592-Chloro-3-p-tolyl-pyrido[2,3-b]pyrazine

Produkt 1

HCID 666655042-Phenyl-3-p-tolyl-pyrido[2,3-b]pyrazine

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Katalysator
2×
HCID 962WaterLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel
HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 2-chloro-3-p-tolyl-pyrido[2,3-b]pyrazine (800 mg, 3.13 mmol), phenylboronic acid (572 mg, 4.69 mmol) and K2CO3 (1297 mg, 9.39 mmol) in dioxane (10 ml) was degassed by bubbling nitrogen through (×3). PdCl2(dppf) (229 mg, 0.313 mmol) was added and the reaction mixture was degassed by bubbling nitrogen through (×3). The resulting mixture was heated using microwave radiation at 150° C. for 2 hours. PdCl2(dppf) (229 mg, 0.313 mmol) was added and the mixture was heated using microwave radiation at 150° C. for 2 hours. After cooling to RT, the mixture was diluted with water and EtOAc, and filtered through Celite® (filter material). The phases were separated and the aqueous extracted with EtOAc The combined organic extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. The crude product was purified by chromatography on silica eluting with 2-5% THF/DCM to give a contaminated gum. The material was re-purified by chromatography on silica eluting with 0-60% EtOAc/iso-hexane to afford the title compound;

Aufarbeitung

  1. customwas degassed
  2. customby bubbling nitrogen through (×3)
  3. customthe reaction mixture was degassed
  4. customby bubbling nitrogen through (×3)
  5. temperatureThe resulting mixture was heated
  6. customat 150° C.
  7. customfor 2 hours
  8. temperaturethe mixture was heated
  9. customat 150° C.
  10. customfor 2 hours
  11. filtrationfiltered through Celite® (filter material)
  12. customThe phases were separated
  13. extractionthe aqueous extracted with EtOAc The combined organic extracts
  14. washwere washed with brine
  15. dry with materialdried over MgSO4
  16. concentrationconcentrated in vacuo
  17. customThe crude product was purified by chromatography on silica eluting with 2-5% THF/DCM
  18. customto give a contaminated gum
  19. customThe material was re-purified by chromatography on silica eluting with 0-60% EtOAc/iso-hexane

Quellen und Nachweise

ORD-Eintrag
ord-da057049df0742799c845eb567e5fb3c
Quelldatensatz
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09132127B2

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