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Cesium carbonate → HCID 89813717, Verbindung

HRID 525356
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 525356
[CH2:1]([C:3]1([CH2:15][CH3:16])[O:7][C:6](=[O:8])[NH:5][C@H:4]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:2].I[C:18]1[CH:36]=[CH:35][C:21]([C:22]([NH:24][C:25]2[CH:26]=[CH:27][CH:28]=[C:29]3[C:34]=2[N:33]=[CH:32][CH:31]=[CH:30]3)=[O:23])=[CH:20][CH:19]=1.C([O-])([O-])=O.[Cs+].[Cs+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.O1CCOCC1>[CH2:15]([C:3]1([CH2:1][CH3:2])[O:7][C:6](=[O:8])[N:5]([C:18]2[CH:36]=[CH:35][C:21]([C:22]([NH:24][C:25]3[CH:26]=[CH:27][CH:28]=[C:29]4[C:34]=3[N:33]=[CH:32][CH:31]=[CH:30]4)=[O:23])=[CH:20][CH:19]=2)[C@H:4]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:16]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 10796Cesium carbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 41661718HCID 41661718, VerbindungHCID 89814220HCID 89814220, Verbindung

Produkt 1

HCID 89813717HCID 89813717, VerbindungAusbeute 7,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysator
HCID 962WaterLösungsmittel
HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a 25 mL round bottom flask were added (S)-5,5-diethyl-4-phenyloxazolidin-2-one (0.3 g, 1.36 mmol), 4-iodo-N-(quinolin-8-yl)benzamide (0.560 g, 1.5 mmol), Cs2CO3 (0.972 g, 3.0 mmol), X-Phos (35 mg, 0.068 mmol), Pd2(dba)3 (62 mg, 0.068 mmol) and 1,4-dioxane (2 mL). The mixture was purged with N2 gas for 15 minutes. The reaction mixture was then heated at 90° C. for 6 hours. After completion of reaction (monitored by TLC, TLC eluent: 30% EtOAc in hexane), the reaction mixture was cooled to ambient temperature and treated with water (5 mL) and the mixture extracted with EtOAc (5 mL). The aqueous layer was back extracted with EtOAc (5 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentrated. The crude material was purified with HPLC (column: AG/AD/C18-027, ramping ACN in H2O, 40-50% B, 0-2 minutes, 50-90% B, 2-10 minutes, flow rate 20 mL/min) to afford 50 mg of (S)-4-(5,5-diethyl-2-oxo-4-phenyloxazolidin-3-yl)-N-(quinolin-8-yl)benzamide as a brown solid. 1H NMR (300 MHz, CDCl3) δ: 10.67 (s, 1H), 8.96-8.80 (m, 2H), 8.20 (dd, J=8.3, 1.6 Hz, 1H), 7.99 (d, J=9 Hz, 2H), 7.68 (d, J=8.7 Hz, 2H), 7.62-7.56 (m, 2H), 7.57-7.47 (m, 1H), 7.40-7.36 (m, 3H), 7.28-7.24 (m, 2H), 5.15 (s, 1H), 2.04-1.96 (m, 2H), 1.39-1.20 (m, 2H), 1.12 (t, J=7.5 Hz, 3H), 0.85 (t, J=7.4 Hz, 3H). m/z (ESI) 466.2 (M+H)+.

Aufarbeitung

  1. customThe mixture was purged with N2 gas for 15 minutes
  2. customAfter completion of reaction (monitored by TLC, TLC eluent: 30% EtOAc in hexane)
  3. temperaturethe reaction mixture was cooled to ambient temperature
  4. extractionthe mixture extracted with EtOAc (5 mL)
  5. extractionThe aqueous layer was back extracted with EtOAc (5 mL)
  6. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  7. concentrationconcentrated
  8. customThe crude material was purified with HPLC (column: AG/AD/C18-027, ramping ACN in H2O, 40-50% B, 0-2 minutes, 50-90% B, 2-10 minutes, flow rate 20 mL/min)

Quellen und Nachweise

ORD-Eintrag
ord-9ba411976d534547b2d850f119b9cb9d
Quelldatensatz
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09340549B2

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