Dimethyl Sulfoxide → HCID 58579028, compound

HRID 2368768Notes

Reaction equation

HRID 2368768 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([N:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1)[CH2:6][CH2:5]2.CS(C)=[O:26].N#N.C1(P([C:53]2[CH:58]=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:59]([OH:61])C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(N(CC)CC)C>[CH2:58]([O:26][C:59]([C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([N:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1)[CH2:6][CH2:5]2)=[O:61])[CH3:53]

Participants

8

Reactant 5

HCID 679Dimethyl SulfoxideHCID 702EthanolHCID 947Nitrogen2×HCID 812191,3-Bis(diphenylphosphino)propaneHCID 58579019HCID 58579019, compound

Product 1

HCID 58579028HCID 58579028, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
100 °C

Procedure

tert-Butyl 4-(5-bromo-2,3-dihydro-1H-inden-1-yl)piperazin-1-carboxylate (11 g, 28.87 mmol) was dissolved in ethanol (50 mL), and dimethyl sulfoxide (5 mL) and triethylamine (5 mL) were added. The system was vacuumized and charged with N2. Palladium acetate (2 g) and 1,3-bis(diphenylphosphino)propane (3 g) were added. The system was vacuumized and charged with N2. The system was vacuumized once again and stirred at 100° C. for 24 hours with inserting CO balloons. After being cooled down to the room temperature, the mixture was filtered by kieselguhr which was then rinsed thoroughly with ethanol. The filtrate was concentrated. The residue was dissolved in ethyl acetate (500 mL) and the solution obtained was washed with brine (3×200 mL), dried over magnesium sulfate, concentrated and finally separated by silica gel column using ethyl acetate/hexanes (1:2 to 1:1) as the eluent to obtain 8.5 g (79% yield) of the subtitle compound. MS (M+1)=375.22.

Workup

  1. temperatureAfter being cooled down to the room temperature
  2. filtrationthe mixture was filtered by kieselguhr which
  3. washwas then rinsed thoroughly with ethanol
  4. concentrationThe filtrate was concentrated
  5. dissolutionThe residue was dissolved in ethyl acetate (500 mL)
  6. customthe solution obtained
  7. washwas washed with brine (3×200 mL)
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated
  10. customfinally separated by silica gel column

Sources & evidence

ORD record
ord-81d23d66c2a2471b9486af048e92cdca
Source dataset
uspto-grants-2014_04
Patent number
US08703771B2

Reaction notes

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