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Potassium Carbonate → HCID 71621529, Verbindung

HRID 2278846
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2278846
Cl[C:2]1[N:7]=[N:6][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[F:24])[N:9]=2)=[N:4][C:3]=1[NH2:25].[CH3:26][C:27]1[C:31](B(O)O)=[C:30]([CH3:35])[O:29][N:28]=1.C(=O)([O-])[O-].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>O1CCOCC1.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]>[CH3:26][C:27]1[C:31]([C:2]2[N:7]=[N:6][C:5]([C:8]3[C:16]4[C:11](=[N:12][CH:13]=[CH:14][CH:15]=4)[N:10]([CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[F:24])[N:9]=3)=[N:4][C:3]=2[NH2:25])=[C:30]([CH3:35])[O:29][N:28]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 75806TricyclohexylphosphineHCID 27343463,5-Dimethylisoxazole-4-boronic acidHCID 89690930HCID 89690930, Verbindung

Produkt 1

HCID 71621529HCID 71621529, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Katalysator
HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Under an argon atmosphere, 140 mg (purity 65%, 0.256 mmol) of 6-chloro-3-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-1,2,4-triazine-5-amine were suspended in 5 ml of absolute dioxane. 154 mg (purity 70%, 0.767 mmol) of (3,5-dimethyl-1,2-oxazol-4-yl)boronic acid, 1.023 ml (1.023 mmol) of 1N aqueous potassium carbonate solution and 14 mg (0.051 mmol) of tricyclohexylphosphine were added and argon was passed through the suspension for 10 min with stirring. Then, 28 mg (0.038 mmol) of 1,1′-bis(diphenylphosphino)ferrocenepalladium(II) chloride were added and the reaction mixture was stirred for 30 min in the microwave at 140° C. The reaction mixture was again stirred for 60 min in the microwave at 140° C. After cooling, the mixture was filtered over an Extrelut cartridge and after-washed with a mixture of dichloromethane/methanol (v/v=20:1). The filtrate was concentrated and the residue was purified by preparative HPLC (mobile phase: acetonitrile/water, gradient 20:80→100:0). This gave 25 mg of the target compound (purity 95%; 18% of theory).

Aufarbeitung

  1. stirringthe reaction mixture was stirred for 30 min in the microwave at 140° C
  2. stirringThe reaction mixture was again stirred for 60 min in the microwave at 140° C
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered over an Extrelut cartridge
  5. washafter-washed with a mixture of dichloromethane/methanol (v/v=20:1)
  6. concentrationThe filtrate was concentrated
  7. customthe residue was purified by preparative HPLC (mobile phase: acetonitrile/water, gradient 20:80→100:0)

Quellen und Nachweise

ORD-Eintrag
ord-0bfc7cc425b94f33802be660b2ba8615
Quelldatensatz
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09133191B2

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