Cesium carbonate → HCID 68457393, compound

HRID 2358398Notes

Reaction equation

HRID 2358398 reaction equation
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.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:53]([O:55][C:56](=[O:77])[CH:57]=[CH:58][C:59]1[CH:64]=[CH:63][C:62]([C:65]([CH3:68])([CH3:67])[CH3:66])=[CH:61][C:60]=1OS(C(F)(F)F)(=O)=O)[CH3:54].[CH3:78][N:79]1[CH2:84][CH2:83][NH:82][CH2:81][CH2:80]1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:53]([O:55][C:56](=[O:77])[CH:57]=[CH:58][C:59]1[CH:64]=[CH:63][C:62]([C:65]([CH3:68])([CH3:67])[CH3:66])=[CH:61][C:60]=1[N:82]1[CH2:83][CH2:84][N:79]([CH3:78])[CH2:80][CH2:81]1)[CH3:54]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 531671-MethylpiperazineHCID 634876Binap, (A+-)-HCID 76587262HCID 76587262, compound

Product 1

HCID 68457393HCID 68457393, compoundYield 73.2%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

Palladium acetate (2.8 mg, 0.013 mmol, 6% mol eq), rac-2,2′-bis(diphenylphosphino)1,1′-binaphthyl (16.2 mg, 0.026 mmol, 12% mol eq), and cesium carbonate (102.6 mg, 0.315 mmol, 1.5 eq) were added in anhydrous toluene under argon atmosphere. After stirring for 5 min, 3-(4-tert-butyl-2-trifluoromethanesulfonyloxyphenyl)acrylic acid ethyl ester (74.0 mg, 0.210 mmol, 1 eq) and N-Methylpiperazine (34.9 μl, 0.315 mmole, 1.5 eq) were added. The mixture was stirred for 24 hr at 80° C. The reaction mixture was purified according to step 1 of Example 22 to give yellow liquid (50.8 mg, 73.2%).

Workup

  1. stirringThe mixture was stirred for 24 hr at 80° C
  2. customThe reaction mixture was purified

Sources & evidence

ORD record
ord-f1197773142348c39cf402f393536a10
Source dataset
uspto-grants-2010_07
Patent number
US07763657B2

Reaction notes

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