Cesium carbonate → HCID 57473700, compound

HRID 1160208Notes

Reaction equation

HRID 1160208 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[O:7]1[CH2:11][CH2:10][NH:9][C:8]1=[O:12].[C:13]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:18]=CC=CC=1P(C1CCCCC1)C1CCCCC1.[CH3:38][N:39]1[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:38][N:39]1[CH2:44][CH2:43][N:42]([C:32]2[CH:33]=[CH:34][C:11]([CH2:10][N:9]3[CH2:18][C@@H:13]([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[O:7][C:8]3=[O:12])=[CH:18][CH:13]=2)[CH2:41][CH2:40]1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 531671-MethylpiperazineHCID 739492-OxazolidinoneHCID 27342162-(Dicyclohexylphosphino)biphenyl

Product 1

HCID 57473700HCID 57473700, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirring suspension of palladium acetate (3 mg, 0.011 mmol), cesium carbonate (103 mg, 0.318 mmol), 3-(4-Iodo-benzyl)-5-(R)-phenyl)-oxazolidin-2-one (40 mg, 0.106 mmol), and Biphenyl-2-yl-dicyclohexyl-phosphane (4 mg, 0.011 mmol) in toluene was added 1-Methyl-piperazine (14 μL, 0.126 mmol). The mixture stirred at 100° C. for 3 hours and was then cooled to room temperature, diluted with water and extracted with ethyl acetate. The organics were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel, eluting with 30-40% ethyl acetate in hexanes. The title compound was isolated as a brown solid (14 mg, 38%). 1H NMR (300 MHz, CDCl3): δ 7.40-7.30 (m, 5H), 7.21 (d, 2H), 6.91 (d, 2H), 5.46 (t, 1H), 4.50-4.31 (q, 2H), 3.76 (t, 1H), 3.30 (t, 1H), 3.27-3.21 (m, 4H), 2.61-2.58 (m, 4H), 2.37 (s, 3H).

Workup

  1. temperaturewas then cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organics were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography on silica gel
  8. washeluting with 30-40% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-f6d82211e32d4ff586ac68e438c47b80
Source dataset
uspto-grants-2010_10
Patent number
US07816354B2

Reaction notes

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