Trimethylsilylacetylene → HCID 53678606, compound

HRID 466734Notes

Reaction equation

HRID 466734 reaction equation
[F:1][C@@H:2]1[C@@H:6]([CH2:7][O:8][C:9]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)=[O:10])[O:5][C@@H:4]([N:18]2[CH:25]=[C:24](I)[C:22](=[O:23])[NH:21][C:19]2=[O:20])[CH2:3]1.[CH3:27][Si:28]([C:31]#[CH:32])([CH3:30])[CH3:29]>C(N(CC)CC)C.CN(C)C=O.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu]I>[F:1][C@@H:2]1[C@@H:6]([CH2:7][O:8][C:9]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)=[O:10])[O:5][C@@H:4]([N:18]2[CH:25]=[C:24]([C:32]#[C:31][Si:28]([CH3:30])([CH3:29])[CH3:27])[C:22](=[O:23])[NH:21][C:19]2=[O:20])[CH2:3]1

Participants

7

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 18648371HCID 18648371, compound

Product 1

HCID 53678606HCID 53678606, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A solution of the product of Stage b), (0.8 g, 1.69 mmoles), bis(triphenylphosphine) palladium (II) chloride (25 mg) and copper (I) iodide (25 mg) in dry triethylamine (40 ml) and N,N-dimethylformamide (3 ml) was degassed thoroughly with nitrogen. (Trimethylsilyl) acetylene (0.47 ml, 3.37 mmoles) was added and the mixture stirred under N2 at 50° for 8 hours. The solvent was removed under reduced pressure, the residue dissolved in methylene chloride (40 ml) and the solution washed with 2% aqueous disodium EDTA solution (4 ml), water (50 ml) and dried (sodium sulphate). Evaporation of the solvent and purification of the residue by silica column chromatography eluting with 2% MeOH/CH2Cl2 afforded the title compound. Trituration with ether/hexane afforded analytically pure title compound as an off-white powder.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue dissolved in methylene chloride (40 ml)
  3. washthe solution washed with 2% aqueous disodium EDTA solution (4 ml), water (50 ml)
  4. dry with materialdried (sodium sulphate)
  5. customEvaporation of the solvent and purification of the residue by silica column chromatography
  6. washeluting with 2% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-70fb651631884407b77b392e45ece73c
Source dataset
uspto-grants-1992_10
Patent number
US05157114

Reaction notes

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