Hydrochloric Acid → HCID 19710212, compound

HRID 725928Notes

Reaction equation

HRID 725928 reaction equation
FC(F)(F)S(O[C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[CH2:12][CH:11]([N:16]([CH2:20][CH2:21][CH3:22])[CH2:17][CH2:18][CH3:19])[CH2:10]2)(=O)=O.[CH:25]([O:27]CCCC)=[CH2:26].C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(N(CC)CC)C>[C:25]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[CH2:12][CH:11]([N:16]([CH2:20][CH2:21][CH3:22])[CH2:17][CH2:18][CH3:19])[CH2:10]2)(=[O:27])[CH3:26]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8108Butyl vinyl etherHCID 812191,3-Bis(diphenylphosphino)propaneHCID 19710221HCID 19710221, compound

Product 1

HCID 19710212HCID 19710212, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-trifluoromethanesulfonyloxy-2-(di-n-propylamino)indan (Example 2) in DMF is treated sequentially with triethylamine, butyl vinyl ether, 1,3-bis(diphenylphosphino)propane, and palladium acetate under nitrogen. The mixture is heated at 80° C. for 0.5 h. (J. Org. Chem. 1990, 55 3654). The reaction mixture is cooled to room temperature and treated with 5% HCl. After stirring for 0.5 h, the mixture is extracted with methylene chloride. The crude product is purified by chromatography to yield the title compound.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. extractionthe mixture is extracted with methylene chloride
  3. customThe crude product is purified by chromatography

Sources & evidence

ORD record
ord-96d943f8ef9e446d94911bd5e0bc43da
Source dataset
uspto-grants-1998_01
Patent number
US05708018

Reaction notes

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