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Potassium Phosphate, Tribasic → 8-Bromo-2-[4-(4-methyl-piperazin-1-yl)-phenyl]-quinoxaline

HRID 216734
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 216734
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9](Cl)[CH:8]=[N:7]2.[CH3:13][N:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:25]=[CH:24][C:23](B3OC(C)(C)C(C)(C)O3)=[CH:22][CH:21]=2)[CH2:16][CH2:15]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:23]1[CH:22]=[CH:21][C:20]([N:17]3[CH2:18][CH2:19][N:14]([CH3:13])[CH2:15][CH2:16]3)=[CH:25][CH:24]=1)[CH:8]=[N:7]2
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 179989051-Methyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazineHCID 593926708-Bromo-2-chloroquinoxaline

Produkt 1

HCID 593928518-Bromo-2-[4-(4-methyl-piperazin-1-yl)-phenyl]-quinoxaline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418476
HCID 178418476, Verbindung
Katalysator

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

A microwave tube is charged with 8-Bromo-2-chloro-quinoxaline (Step 1.4, 2.5 g, 10.267 mmol), 1-Methyl-4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-piperazine (2.88 g, 9.24 mmol), K3PO4 (6.67 g, 30.8 mmol) and PdCl2(PPh3)2 (221 mg, 0.308 mmol). After several cycles of vacuum/purge with argon, a mixture of 21 ml of DMA and 560 μl deionized water is added. The reaction mixture is then heated to 105° C. for 4 h. After cooling, the suspension is poured onto de-ionized water and diluted with EtOAc. The phases are separated and the aqueous phase re-extracted twice with EtOAc. The combined organic phases are washed with saturated brine and dried over Na2SO4. After filtration, the mixture is concentrated in vacuo. The residue is purified by chromatography (silicagel, CH2Cl2:EtOH:NH3 95:4.5:0.5 from 1:0=>0:1) to afford the title compound as a yellow orange solid, Rt=0.930 min (Acquity HPLC BEH C18, 2.1×50 mm, 1.7 micron, detection 215 nM, 0.1 min 2% CH3CN in H2O, 2% to 100% CH3CN in H2O in 1.5 min, 0.4 min 100% CH3CN+0.1% TFA, flow rate 1.0 ml/min); MS: 383 (M+1, 79Br)+.

Aufarbeitung

  1. customAfter several cycles of vacuum/purge with argon
  2. additiona mixture of 21 ml of DMA and 560 μl
  3. additionis added
  4. temperatureAfter cooling
  5. additionthe suspension is poured onto de-ionized water
  6. additiondiluted with EtOAc
  7. customThe phases are separated
  8. extractionthe aqueous phase re-extracted twice with EtOAc
  9. washThe combined organic phases are washed with saturated brine
  10. dry with materialdried over Na2SO4
  11. filtrationAfter filtration
  12. concentrationthe mixture is concentrated in vacuo
  13. customThe residue is purified by chromatography (silicagel, CH2Cl2:EtOH:NH3 95:4.5:0.5 from 1:0=>0:1)

Quellen und Nachweise

ORD-Eintrag
ord-677e6774131b4fbc93c2d1942dfed7de
Quelldatensatz
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08193189B2

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