HCID 22714700, compound → HCID 22714702, compound

HRID 351919Notes

Reaction equation

HRID 351919 reaction equation
F[C:2](F)(F)[C:3]([C:5]1[C:10]2[CH:11]([C:13]#[N:14])[CH2:12][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4]>N1C=CC=CC=1>[C:3]([C:5]1[C:10]2[CH:11]([C:13]#[N:14])[CH2:12][C:9]=2[CH:8]=[CH:7][CH:6]=1)(=[O:4])[CH3:2]

Participants

3

Reactant 1

HCID 22714700HCID 22714700, compound

Product 1

HCID 22714702HCID 22714702, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution composed of 55.94 g of 6-trifluoroacetyl-1-benzocyclobutanecarbonitrile in 600 ml of pyridine is purged with nitrogen for 15 minutes; 30.5 ml of triethylamine, 117.44 ml of butyl vinyl ether, 2.25 g of 1,3-bis-(diphenylphosphino)propane and 1.02 g of palladium acetate are added and the reaction mixture is heated at reflux for 2 hours. 400 ml of 1N hydrochloric acid are then added dropwise in the course of 1 hour and, after stirring for 3 hours at ambient temperature, the reaction mixture is extracted with ether. The organic phases are washed, dried and concentrated to yield a residue, which is purified by chromatography on silica gel (dichloromethane: 100%) allowing the expected product to be isolated.

Workup

  1. customis purged with nitrogen for 15 minutes
  2. addition30.5 ml of triethylamine, 117.44 ml of butyl vinyl ether, 2.25 g of 1,3-bis-(diphenylphosphino)propane and 1.02 g of palladium acetate are added
  3. temperaturethe reaction mixture is heated
  4. temperatureat reflux for 2 hours
  5. addition400 ml of 1N hydrochloric acid are then added dropwise in the course of 1 hour
  6. extractionthe reaction mixture is extracted with ether
  7. washThe organic phases are washed
  8. customdried
  9. concentrationconcentrated
  10. customto yield a residue, which
  11. customis purified by chromatography on silica gel (dichloromethane: 100%)
  12. customto be isolated

Sources & evidence

ORD record
ord-434b9a52892548d39ae3ec1eb86718b2
Source dataset
uspto-grants-2004_06
Patent number
US06743818B2

Reaction notes

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