Trimethylsilylacetylene → HCID 18629998, compound

HRID 725561Notes

Reaction equation

HRID 725561 reaction equation
[Cl:1][C:2]1[C:12](I)=[CH:11][CH:10]=[C:9]([Si:14]([CH3:17])([CH3:16])[CH3:15])[C:3]=1[C:4]([NH:6][CH2:7][CH3:8])=[O:5].[CH3:18][Si:19]([C:22]#[CH:23])([CH3:21])[CH3:20]>C(N(CC)CC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:1][C:2]1[C:12]([C:23]#[C:22][Si:19]([CH3:21])([CH3:20])[CH3:18])=[CH:11][CH:10]=[C:9]([Si:14]([CH3:17])([CH3:16])[CH3:15])[C:3]=1[C:4]([NH:6][CH2:7][CH3:8])=[O:5]

Participants

5

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 10523923HCID 10523923, compound

Product 1

HCID 18629998HCID 18629998, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

To a slurry of the compound of Example 239 (0.763 g, 2.0 mmol), bis(triphenylphosphine)palladium dichloride (28 mg, 0.04 mmol) and cuprous iodide (15 mg, 0.08 mmol) in anhydrous triethylamine (10 mL) was added trimethylsilylacetylene (0.236 g, 2.4 mmol). The brown slurry was stirred at RT for 3.5 h, concentrated, slurried in ether and filtered through silica gel (ether). The crude product was further purified by flash chromatography (ethyl acetate/hexanes) followed by recrystallization from hexanes to afford the title compound as white crystals (0.618 g, 88%). m.p. 131°-132° C.

Workup

  1. concentrationconcentrated
  2. filtrationfiltered through silica gel (ether)
  3. customThe crude product was further purified by flash chromatography (ethyl acetate/hexanes)
  4. customfollowed by recrystallization from hexanes

Sources & evidence

ORD record
ord-9e8c32de5c2e4ddab837cdb169117c68
Source dataset
uspto-grants-1998_01
Patent number
US05705513

Reaction notes

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