Cesium carbonate → HCID 86603657, compound

HRID 226346Notes

Reaction equation

HRID 226346 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:67][C:68]1[CH:81]=[CH:80][C:71]([C:72]([N:74]2[CH2:78][CH2:77][C@@H:76]([NH2:79])[CH2:75]2)=[O:73])=[CH:70][CH:69]=1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:67][C:68]1[CH:81]=[CH:80][C:71]([C:72]([N:74]2[CH2:78][CH2:77][C@@H:76]([NH:79][C:2]3[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=3)[CH2:75]2)=[O:73])=[CH:70][CH:69]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 688115Ethyl trans-4-BromocinnamateHCID 68963176(3R)-1-(4-chlorobenzoyl)-3-pyrrolidinamine

Product 1

HCID 86603657HCID 86603657, compoundYield 63.3%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of ethyl (2E)-3-(4-bromophenyl)acrylate (300 mg) in toluene (3 mL) was added palladium(II) acetate (26.4 mg), (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (110 mg), cesium carbonate (583 mg), and (3R)-1-(4-chlorobenzoyl)-3-pyrrolidinamine (291 mg). The mixture was heated at 90° C. for 2 days. The resulting mixture was poured into sat.NH4Cl aq solution and extracted with AcOEt. The organic layer was washed with sat. NH4Cl ag solution, water, and brine, and dried over Na2SO4. The solvent was removed in vacuo and residual brown oil was purified by preparative thin layer chromatography (chloroform methanol=95:5) to give ethyl (2E)-3-(4-{[(3R)-1-(4-chlorobenzoyl)-3-pyrrolidinyl]amino}phenyl)acrylate (297 mg) as pale yellow form.

Workup

  1. additionThe resulting mixture was poured
  2. extractionNH4Cl aq solution and extracted with AcOEt
  3. washThe organic layer was washed with sat. NH4Cl ag solution, water, and brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed in vacuo and residual brown oil
  6. customwas purified by preparative thin layer chromatography (chloroform methanol=95:5)

Sources & evidence

ORD record
ord-2ff0bd2255694e7a852897cada5bd623
Source dataset
uspto-grants-2009_07
Patent number
US07557127B2

Reaction notes

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