Cesium carbonate → HCID 69677648, compound

HRID 1816768Notes

Reaction equation

HRID 1816768 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.[CH3:53][C@H:54]1[O:59][C@@H:58]([CH3:60])[CH2:57][N:56]([C:61]2[CH:66]=[CH:65][C:64]([C:67]3[CH:72]=[CH:71][C:70](OS(C(F)(F)F)(=O)=O)=[CH:69][CH:68]=3)=[CH:63][CH:62]=2)[CH2:55]1.[N:81]1([C:87]2[CH:97]=[CH:96][C:90]([C:91]([O:93][CH2:94][CH3:95])=[O:92])=[CH:89][CH:88]=2)[CH2:86][CH2:85][NH:84][CH2:83][CH2:82]1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH2:94]([O:93][C:91](=[O:92])[C:90]1[CH:89]=[CH:88][C:87]([N:81]2[CH2:82][CH2:83][N:84]([C:70]3[CH:71]=[CH:72][C:67]([C:64]4[CH:65]=[CH:66][C:61]([N:56]5[CH2:57][C@H:58]([CH3:60])[O:59][C@H:54]([CH3:53])[CH2:55]5)=[CH:62][CH:63]=4)=[CH:68][CH:69]=3)[CH2:85][CH2:86]2)=[CH:97][CH:96]=1)[CH3:95]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 2761178Ethyl 4-(piperazin-1-yl)benzoateHCID 53981212HCID 53981212, compound

Product 1

HCID 69677648HCID 69677648, compoundYield 74.8%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of cesium carbonate (1.43 g), palladium(II) acetate (35 mg) and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (146 mg) in dioxane (6 ml) was successively added trifluoromethanesulfonic acid 4′-(cis-2,6-dimethylmorpholin-4-yl)-1,1′-biphenyl-4-yl ester (1.30 g) and ethyl 4-piperazinylbenzoate (0.88 g) in a stream of nitrogen. The mixture was stirred at ambient temperature for 30 minutes and at 100° C. for further 6.5 hours. After cooling to room temperature, water was added to the reaction mixture. The resulting precipitates were filtered, washed with water and dried. The residue was pulverized with acetone and collected by filtration to give 4-[4-[4′-(cis-2,6-dimethylmorpholin-4-yl)-1,1′-biphenyl-4-yl]piperazinyl]benzoic acid ethyl ester (1.17 g).

Workup

  1. temperatureAfter cooling to room temperature
  2. customThe resulting precipitates
  3. filtrationwere filtered
  4. washwashed with water
  5. customdried
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-aec4320a6b22499f92b87ea19675e134
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

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