Cesium carbonate → HCID 178497514, compound

HRID 1816354Notes

Reaction equation

HRID 1816354 reaction equation
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

Participants

9

Reactant 4

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

Product 1

HCID 178497514HCID 178497514, compoundYield 53,562.699%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
110 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-0f2b2b9e924140c1be1f484564735b53
Source dataset
uspto-grants-2005_04
Patent number
US06884774B2

Reaction notes

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