Triphenylphosphine → HCID 19895647, compound

HRID 1073969Notes

Reaction equation

HRID 1073969 reaction equation
I[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:27][C:28]([CH3:40])([O:31][C:32]1[CH:39]=[CH:38][C:35]([C:36]#[N:37])=[CH:34][CH:33]=1)[C:29]#[CH:30]>C(NCC)C.[Pd](Cl)Cl.[Cu]I>[CH3:27][C:28]([CH3:40])([O:31][C:32]1[CH:33]=[CH:34][C:35]([C:36]#[N:37])=[CH:38][CH:39]=1)[C:29]#[C:30][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 11776TriphenylphosphineHCID 707143-IodopyridineHCID 27790724-[(2-Methylbut-3-yn-2-yl)oxy]benzonitrile

Product 1

HCID 19895647HCID 19895647, compound

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8021DiethylamineSolvent

Procedure

10.25 g of 3-iodopyridine were added at to a solution of 44 mg of palladium(II) chloride, room temperature 131 mg of triphenylphosphine and 95 mg of copper(I) iodide in 200 mg of diethylamine 9.25 g of 4-(1,1-dimethyl-2-propynyloxy)benzonitrile were then added and the mixture was stirred for 3 days. The mixture was evaporated and the residue was partitioned between ethyl acetate and water. The organic phase was dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using ethyl acetate/petroleum ether (11:9) for the elution to give 11.8 g of 4-[1,1-dimethyl-3-(3-pyridyl)-2-propynyloxy]benzonitrile in the form of an oil.

Workup

  1. additionwere then added
  2. customThe mixture was evaporated
  3. customthe residue was partitioned between ethyl acetate and water
  4. dry with materialThe organic phase was dried over sodium sulphate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel
  7. washfor the elution

Sources & evidence

ORD record
ord-222372a8b5f64169bb8e1d385375dbc6
Source dataset
uspto-grants-1990_11
Patent number
US04971982

Reaction notes

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