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Sodium Carbonate → 3-(6-Amino-1,7-naphthyridin-8-yl)benzonitrile

HRID 2376626
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2376626
C(=O)([O-])[O-].[Na+].[Na+].[NH2:7][C:8]1[CH:9]=[C:10]2[C:15](=[C:16](Br)[N:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:38]([C:40]1[CH:41]=[C:42](B(O)O)[CH:43]=[CH:44][CH:45]=1)#[N:39]>C1COCC1>[NH2:7][C:8]1[CH:9]=[C:10]2[C:15](=[C:16]([C:44]3[CH:43]=[CH:42][CH:41]=[C:40]([C:38]#[N:39])[CH:45]=3)[N:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 27343253-Cyanophenylboronic acidHCID 107043358-Bromo-1,7-naphthyridin-6-amine

Produkt 1

HCID 107055713-(6-Amino-1,7-naphthyridin-8-yl)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a mixture of THF (80 ml) and 2N sodium carbonate (34 ml, aqueous) is added 6-amino-8-bromo-1,7-naphthyridine (4.007 g), triphenylphosphine (0.37 g) and 3-cyanophenyl-boronic acid (3.23 g). The mixture is degassed under argon three times and then bis(di-benzylidene-acetone)palladium (0) (0.4 g) is added and the mixture is degassed under argon three more times. The mixture is heated at 80° C. under argon for 16 hours then cooled and filtered. The mixture is diluted with ethyl acetate and washed with 2N sodium hydroxide then brine. After drying over sodium sulfate the organic layer is evaporated and suspended in ether. The solid precipitate thus obtained is the title compound, which is filtered off.

Aufarbeitung

  1. customThe mixture is degassed under argon three times
  2. additionbis(di-benzylidene-acetone)palladium (0) (0.4 g) is added
  3. customthe mixture is degassed under argon three more times
  4. temperaturethen cooled
  5. filtrationfiltered
  6. additionThe mixture is diluted with ethyl acetate
  7. washwashed with 2N sodium hydroxide
  8. dry with materialAfter drying over sodium sulfate the organic layer
  9. customis evaporated
  10. customThe solid precipitate thus obtained

Quellen und Nachweise

ORD-Eintrag
ord-1f9798692d644766ae1f77ba5d3e54ab
Quelldatensatz
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07468370B2

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