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Potassium Phosphate, Tribasic → HCID 46865529, Verbindung

HRID 216733
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 216733
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[CH:16][C:15]([N:18]3[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]3)=[CH:14][CH:13]=1)[CH:8]=[N:7]2.[F:25][C:26]1[CH:38]=[C:37](B2OC(C)(C)C(C)(C)O2)[CH:36]=[C:35]([F:48])[C:27]=1[CH2:28][N:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CC([O-])=O.CC([O-])=O.[Pd+2]>[F:48][C:35]1[CH:36]=[C:37]([C:2]2[CH:3]=[CH:4][CH:5]=[C:6]3[C:11]=2[N:10]=[C:9]([C:12]2[CH:17]=[CH:16][C:15]([N:18]4[CH2:19][CH2:20][N:21]([CH3:24])[CH2:22][CH2:23]4)=[CH:14][CH:13]=2)[CH:8]=[N:7]3)[CH:38]=[C:26]([F:25])[C:27]=1[CH2:28][N:29]1[CH2:30][CH2:31][O:32][CH2:33][CH2:34]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 59392637HCID 59392637, VerbindungHCID 593928518-Bromo-2-[4-(4-methyl-piperazin-1-yl)-phenyl]-quinoxaline

Produkt 1

HCID 46865529HCID 46865529, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 167845palladium(II) acetateKatalysator

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

A microwave tube is charged with 8-Bromo-2-[4-(4-methyl-piperazin-1-yl)-phenyl]-quinoxaline (2.6 g, 6.783 mmol), 4-[2,6-Difluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyl]-morpholine (Step 87.1, 2.68 g, 7.12 mmol), S-Phos (258 mg, 0.611 mmol), K3PO4 (4.41 g, 20.4 mmol) and Pd(OAc)2 (45.68 mg, 0.203 mmol). After several cycles of vacuum/purge with argon, a mixture of 370 μl deionized water in 30 ml 1,2-dimethoxy-ethane is added. The reaction mixture is then heated to 105° C. for 12 h. After cooling, the reaction mixture is diluted with CH2Cl2, poured onto a saturated solution of NaHCO3 and extracted 3× with CH2Cl2. The combined organic layers are washed with water, brine, dried over Na2SO4, filtered and the filtrate is concentrated in vacuo. The residue is purified by chromatography (silicagel, CH2Cl2/CH2Cl2:EtOH:NH3 90:9:1 4:6) to afford the title compound as yellow solid, Rt=0.742 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: 516 (M+1)+.

Aufarbeitung

  1. customAfter several cycles of vacuum/purge with argon
  2. additiona mixture of 370 μl
  3. additionis added
  4. temperatureAfter cooling
  5. additionthe reaction mixture is diluted with CH2Cl2
  6. additionpoured onto a saturated solution of NaHCO3
  7. extractionextracted 3× with CH2Cl2
  8. washThe combined organic layers are washed with water, brine
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. concentrationthe filtrate is concentrated in vacuo
  12. customThe residue is purified by chromatography (silicagel, CH2Cl2/CH2Cl2:EtOH:NH3 90:9:1 4:6)

Quellen und Nachweise

ORD-Eintrag
ord-f0aae2382e9f40c5b6d8a433aec385c7
Quelldatensatz
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08193189B2

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