Cesium carbonate → HCID 11352447, Verbindung

HRID 2357886Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2357886
C(=O)([O-])[O-].[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.[C:53]1([CH2:59][CH2:60][CH2:61][NH:62][C:63]([C:65]2[N:70]=[CH:69][C:68](OS(C(F)(F)F)(=O)=O)=[CH:67][CH:66]=2)=[O:64])[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1.[N:79]1([C:85]([C:87]2[CH:92]=[CH:91][CH:90]=[CH:89][C:88]=2[C:93]([F:96])([F:95])[F:94])=[O:86])[CH2:84][CH2:83][NH:82][CH2:81][CH2:80]1>C1(C)C=CC=CC=1.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[C:53]1([CH2:59][CH2:60][CH2:61][NH:62][C:63]([C:65]2[CH:66]=[CH:67][C:68]([N:82]3[CH2:83][CH2:84][N:79]([C:85](=[O:86])[C:87]4[CH:92]=[CH:91][CH:90]=[CH:89][C:88]=4[C:93]([F:96])([F:94])[F:95])[CH2:80][CH2:81]3)=[CH:69][N:70]=2)=[O:64])[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=1

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 167337841-[2-(Trifluoromethyl)benzoyl]piperazineHCID 86609725Trifluoromethanesulfonic acid 6-(3-phenylpropylcarbamoyl)pyridin-3-yl ester

Produkt 1

HCID 11352447HCID 11352447, VerbindungAusbeute 13 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

A 50-mL flask was charged with cesium carbonate (0.078 g, 0.238 mmol), palladium diacetate (0.0019 g, 0.0085 mmol) and BINAP (0.0079 g, 0.013 mmol) and flushed with argon for 30 minutes. A solution of trifluoromethanesulfonic acid 6-(3-phenylpropylcarbamoyl)pyridin-3-yl ester (0.066 g, 0.17 mmol) and piperazin-1-yl-(2-trifluoromethylphenyl)methanone (0.053 g, 0.20 mmol) in toluene (2 mL) was added via syringe. The reaction mixture was heated at 100 C for 26 h, cooled to room temperature, diluted with toluene (20 mL), filtered and concentrated in vacuo. The crude product was purified by column chromatography to afford the title compound as a white solid (0.011 g, 13% yield). 1H NMR (300 MHz, CDCl3) δ 8.15, 8.04, 7.85, 7.74, 7.50-7.65, 7.36, 7.30-7.10, 3.90-4.10, 3.55-3.30, 3.22, 2.72, 1.96. MS (ES+) m/z 497.4 (M+1).

Aufarbeitung

  1. customflushed with argon for 30 minutes
  2. temperatureThe reaction mixture was heated at 100 C for 26 h
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-40895d12926e4440adca47a06a901218
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07763618B2

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