Cesium carbonate → HCID 67107114, compound

HRID 1623663Notes

Reaction equation

HRID 1623663 reaction equation
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.[CH2:53]([O:60][C:61]1[CH:76]=[CH:75][C:74](Br)=[CH:73][C:62]=1[C:63]([O:65][CH2:66][C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1)=[O:64])[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1.[CH3:78][N:79]1[CH2:84][CH2:83][NH:82][CH2:81][CH2:80]1>CCOCC.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].C1(C)C=CC=CC=1>[CH3:78][N:79]1[CH2:84][CH2:83][N:82]([C:74]2[CH:75]=[CH:76][C:61]([O:60][CH2:53][C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)=[C:62]([CH:73]=2)[C:63]([O:65][CH2:66][C:67]2[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=2)=[O:64])[CH2:81][CH2:80]1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 531671-MethylpiperazineHCID 634876Binap, (A+-)-HCID 17750009Benzyl 2-(benzyloxy)-5-bromobenzoate

Product 1

HCID 67107114HCID 67107114, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

Caesium carbonate (574 mg, 1.76 mmol) was finely ground in a nitrogen-filled glovebox and weighed into an oven-dried Schlenk flask. The flask was quickly capped with a rubber septum and purged with argon. Pd2(dba)3 (2.88 mg, 3.15 μmol) and BINAP (5.88 mg, 9.44 μmol) were added into the flask, followed by benzyl 2-(benzyloxy)-5-bromobenzoate (may be prepared as described in Description 4; 500 mg, 1.26 mmol), 1-methylpiperazine (126 mg, 1.26 mmol), and toluene (10 ml). The solution was refluxed for 10 h. The solution was then cooled to room temperature, diluted with ether, filtered, and concentrated in vacuo to yield the title compound which was not further purified. 100 mg.

Workup

  1. additionfilled glovebox
  2. customweighed into an oven-dried Schlenk flask
  3. customThe flask was quickly capped with a rubber septum
  4. custompurged with argon
  5. temperatureThe solution was refluxed for 10 h
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-25f414b69fd044109e14aceced4ca57d
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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