Cesium carbonate → HCID 178497514, Verbindung

HRID 1816354Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1816354
C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.FC(F)(F)S(O[C:59]1[CH:64]=[CH:63][C:62]([C:65]2[CH:70]=[CH:69][C:68]([C:71]([O:73][CH3:74])=[O:72])=[CH:67][CH:66]=2)=[CH:61][CH:60]=1)(=O)=O.[CH:77]1([C@H:83]2[CH2:88][CH2:87][C@H:86]([N:89]3[CH2:94][CH2:93][NH:92][CH2:91][CH2:90]3)[CH2:85][CH2:84]2)[CH2:82][CH2:81][CH2:80][CH2:79][CH2:78]1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.ClCCl.O>[CH:77]1([C@H:83]2[CH2:88][CH2:87][C@H:86]([N:89]3[CH2:90][CH2:91][N:92]([C:59]4[CH:64]=[CH:63][C:62]([C:65]5[CH:70]=[CH:69][C:68]([C:71]([O:73][CH3:74])=[O:72])=[CH:67][CH:66]=5)=[CH:61][CH:60]=4)[CH2:93][CH2:94]3)[CH2:85][CH2:84]2)[CH2:78][CH2:79][CH2:80][CH2:81][CH2:82]1

Komponenten

9

Edukt 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 22492882Methyl 4'-(trifluoromethanesulfonyloxy)-[1,1'-biphenyl]-4-carboxylateHCID 178420292HCID 178420292, Verbindung

Produkt 1

HCID 178497514HCID 178497514, VerbindungAusbeute 53.562,699 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a mixture of cesium carbonate (2.54 g), palladium(II) acetate (62 mg) and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (260 mg) in toluene (6 ml) was successively added methyl 4′-trifluoromethylsulfonyloxy-1,1′-biphenyl-4-carboxylate (1 g) and 1-(trans-4-cyclohexylcyclohexyl)-piperazine (835 mg) in stream of nitrogen. The mixture was stirred at ambient temperature for 45 minutes and at 110° C. for further 23 hours. After cooling to room temperature, water and dichloromethane was added to the reaction mixture. The resulting precipitate was collected by filtration and washed with water and dried to give methyl 4′-[4-(trans-4-cyclohexylcyclohexyl)-1-piperazinyl]-1,1′-biphenyl-4-carboxylate (684.8 g).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-0f2b2b9e924140c1be1f484564735b53
Quelldatensatz
uspto-grants-2005_04
Patentnummer
US06884774B2

Notizen zur Reaktion

Wird geladen…