(3-Aminopropyl)triethoxysilane → HCID 178476782, compound

HRID 420098Notes

Reaction equation

HRID 420098 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.[PH2:12]([O-:14])=[O:13].[NH3+][C:16]1C=CC=C[CH:17]=1.NCCC[Si](OCC)(OCC)OCC.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(#N)C.C(OCC)(=O)C.Cl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:9][C:8]([F:11])([F:10])[C:5]1[CH:6]=[CH:7][C:2]([PH:12](=[O:14])[O:13][CH2:16][CH3:17])=[CH:3][CH:4]=1

Participants

9

Reactant 4

HCID 13521(3-Aminopropyl)triethoxysilaneHCID 67993Benzene, 1-iodo-4-(trifluoromethyl)-HCID 812191,3-Bis(diphenylphosphino)propaneHCID 178527020HCID 178527020, compound

Product 1

HCID 178476782HCID 178476782, compoundYield 28%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 313Hydrochloric AcidSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a degassed solution of 4-iodobenzotrifluoride (4.70 g, 17.2 mmol), anilinium hypophosphite (3.51 g, 22.1 mmol), and 3-aminopropyl triethoxysilane (4.88 g, 22.1 mmol) in anhydrous acetonitrile (110 mL) were added palladium acetate (82.5 mg, 0.367 mmol, 2 mol %) and 1,3-bis(diphenylphosphino)propane (167 mg, 0.404 mol, 2.2 mol %). The mixture was heated under reflux for 32 hrs, then cooled down to room temperature, diluted with ethyl acetate and hydrochloric acid (IM) and partitioned. The aqueous layer was further extracted with ethyl acetate, and the combined extracts were washed with aqueous sodium hydrogen carbonate and brine and dried over magnesium sulfate. The solvent was removed in vacuo and the residue was purified by column chromatography using 25 to 100% ethyl acetate in petroleum ether. Further purification by distillation afforded compound AZ1 (1.14 g) in 28% yield.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 32 hrs
  3. custompartitioned
  4. extractionThe aqueous layer was further extracted with ethyl acetate
  5. washthe combined extracts were washed with aqueous sodium hydrogen carbonate and brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed in vacuo
  8. customthe residue was purified by column chromatography
  9. customFurther purification
  10. distillationby distillation
  11. customafforded compound AZ1 (1.14 g) in 28% yield

Sources & evidence

ORD record
ord-5b6d117b552d4e7c892d8dde9ed0d3c0
Source dataset
uspto-grants-2012_01
Patent number
US08093379B2

Reaction notes

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