StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Potassium Phosphate, Tribasic → HCID 9836526, Verbindung

HRID 586237
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 586237
Br[C:2]1[N:6]2[N:7]=[CH:8][CH:9]=[N:10][C:5]2=[N:4][CH:3]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[F:19][C:20]1[CH:25]=[CH:24][C:23](B2OC(C)(C)C(C)(C)O2)=[CH:22][C:21]=1[C:35]1[C:36]([C:41]#[N:42])=[CH:37][CH:38]=[CH:39][CH:40]=1>CN(C)C(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:19][C:20]1[CH:25]=[CH:24][C:23]([C:2]2[N:6]3[N:7]=[CH:8][CH:9]=[N:10][C:5]3=[N:4][CH:3]=2)=[CH:22][C:21]=1[C:35]1[C:36]([C:41]#[N:42])=[CH:37][CH:38]=[CH:39][CH:40]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 117716472′-Fluoro-5′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)[1,1′-biphenyl]-2-carbonitrileHCID 223295537-Bromoimidazo[1,2-b][1,2,4]triazine

Produkt 1

HCID 9836526HCID 9836526, VerbindungAusbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A stirred mixture of 7-bromoimidazo[1,2-b][1,2,4]triazine (0.22 g, 1.105 mmol), dried potassium phosphate (0.425 g, 2.002 mmol) and 2′-fluoro-5′-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-biphenyl-2-carbonitrile (0.649 g, 2.008 mmol) in anhydrous N,N-dimethylacetamide (4 ml) was degassed by evacuation and refilling with nitrogen three times. Tetrakis(triphenylphosphine)palladium(0) (0.058 g, 0.05 mmol) was added and the mixture was degassed with two more evacuation-refilling cycles before heating at 80° C. for 4.5 h. The mixture was cooled to ambient temperature, diluted with ethyl acetate and filtered. The filtrate was washed with brine (200 ml), and the aqueous portion extracted with more ethyl acetate. The combined organic extracts were dried (Na2SO4) and evaporated in vacuo. The residue was purified by chromatography (silica gel, EtOAc) then recrystallisation (EtOAc) to give 74 mg (24%) of the title compound: mp 211-215° C.; 1H NMR (360 MHz, CDCl3) δ 7.36-7.41 (1H, t, J 7.2 Hz), 7.53-7.61 (2H, m), 7.70-7.74 (1H, m), 7.83 (1H, d, J 7.7 Hz), 8.12-8.16 (2H, m), 8.35 (1H, s), 8.50 (1H, dd, J 2.1, 11.6 Hz); MS (ES+) m/z 316 [M+H]+.

Aufarbeitung

  1. customwas degassed by evacuation and refilling with nitrogen three times
  2. customthe mixture was degassed with two more evacuation-refilling cycles
  3. temperatureThe mixture was cooled to ambient temperature
  4. additiondiluted with ethyl acetate
  5. filtrationfiltered
  6. washThe filtrate was washed with brine (200 ml)
  7. extractionthe aqueous portion extracted with more ethyl acetate
  8. dry with materialThe combined organic extracts were dried (Na2SO4)
  9. customevaporated in vacuo
  10. customThe residue was purified by chromatography (silica gel, EtOAc)
  11. customrecrystallisation (EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-4340d1fbc6344b4783ed487004061b84
Quelldatensatz
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06936608B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion