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Potassium Phosphate, Tribasic → (4-Ethyl-piperazin-1-yl)-(2-methyl-4-{8-[3-methyl-4-(1-methyl-1-morpholin-4-yl-ethyl)-phenyl]-quinoxalin-2-yl}-phenyl)-methanone

HRID 216731
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 216731
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]([C:18]([N:20]3[CH2:25][CH2:24][N:23]([CH2:26][CH3:27])[CH2:22][CH2:21]3)=[O:19])=[C:14]([CH3:28])[CH:13]=1)[CH:8]=[N:7]2.[CH3:29][C:30]([N:48]1[CH2:53][CH2:52][O:51][CH2:50][CH2:49]1)([C:32]1[CH:37]=[CH:36][C:35](B2OC(C)(C)C(C)(C)O2)=[CH:34][C:33]=1[CH3:47])[CH3:31].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]>[CH2:26]([N:23]1[CH2:24][CH2:25][N:20]([C:18]([C:15]2[CH:16]=[CH:17][C:12]([C:9]3[CH:8]=[N:7][C:6]4[C:11](=[C:2]([C:35]5[CH:36]=[CH:37][C:32]([C:30]([CH3:29])([N:48]6[CH2:53][CH2:52][O:51][CH2:50][CH2:49]6)[CH3:31])=[C:33]([CH3:47])[CH:34]=5)[CH:3]=[CH:4][CH:5]=4)[N:10]=3)=[CH:13][C:14]=2[CH3:28])=[O:19])[CH2:21][CH2:22]1)[CH3:27]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 593927364-{1-Methyl-1-[2-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethyl}-morpholineHCID 59392849HCID 59392849, Verbindung

Produkt 1

HCID 59392650
(4-Ethyl-piperazin-1-yl)-(2-methyl-4-{8-[3-methyl-4-(1-methyl-1-morpholin-4-yl-ethyl)-phenyl]-quinoxalin-2-yl}-phenyl)-methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 167845palladium(II) acetateKatalysator

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

A microwave tube is charged with of [4-(8-Bromo-quinoxalin-2-yl)-2-methyl-phenyl]-(4-ethyl-piperazin-1-yl)-methanone (step 80.1, 49 mg, 0.112 mmol), 4-{1-Methyl-1-[2-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethyl}-morpholine (40.4 mg, ca. 0.117 mmol), S-Phos (4.25 mg, 0.01 mmol), K3PO4 (72.5 mg, 0.33 mmol) and Pd(OAc)2 (0.75 mg, 0.0033 mmol). After several cycles of vacuum/purge with argon, 3 ml of a mixture consisting of 28 μl deionized water in 12 ml 1,2-dimethoxy-ethane, are added. The reaction mixture is then heated to 105° C. for 5 h 30. After cooling, the reaction mixture is diluted with CH2Cl2, poured onto a saturated solution of Na2CO3 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 from 1:0=>0:1) to afford the title compound as a pale yellow foam, Rt=1.777 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: 578 (M+1)+.

Aufarbeitung

  1. customAfter several cycles of vacuum/purge with argon, 3 ml of a mixture
  2. additionare added
  3. temperatureAfter cooling
  4. additionthe reaction mixture is diluted with CH2Cl2
  5. additionpoured onto a saturated solution of Na2CO3
  6. extractionextracted 3× with CH2Cl2
  7. washThe combined organic layers are washed with water, brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationthe filtrate is concentrated in vacuo
  11. customThe residue is purified by chromatography (silicagel, CH2Cl2/CH2Cl2:EtOH:NH3 90:9:1 from 1:0=>0:1)

Quellen und Nachweise

ORD-Eintrag
ord-f3d944400ae347e39577b524ce169ba5
Quelldatensatz
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08193189B2

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