Trimethylsilylacetylene → 2-Fluoro-3-((trimethylsilyl)ethynyl)pyridine

HRID 362219Notes

Reaction equation

HRID 362219 reaction equation
[F:1][C:2]1[C:7](I)=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:9][Si:10]([C:13]#[CH:14])([CH3:12])[CH3:11]>C1COCC1.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>[F:1][C:2]1[C:7]([C:14]#[C:13][Si:10]([CH3:12])([CH3:11])[CH3:9])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 70095012-Fluoro-3-iodopyridine

Product 1

HCID 539803832-Fluoro-3-((trimethylsilyl)ethynyl)pyridineYield 94.6%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 2-fluoro-3-iodopyridine (5 g), trimethylsilylacetylene (2.86 g) copper(I) iodide (0.015 g) and bis(triphenylphosphine)palladium dichloride (0.06 g) in a mixture of THF (20 mL) and triethylamine (30 mL) was stirred under argon for 4 hours. The solvents were evaporated and the residue was taken up in water/ethyl acetate. The organic phase was separated, dried and evaporated. Distillation of the residue gave 2-fluoro-3-(trimethylsilylethynyl)pyridine as an oil (4.10 g).

Workup

  1. customThe solvents were evaporated
  2. customThe organic phase was separated
  3. customdried
  4. customevaporated
  5. distillationDistillation of the residue

Sources & evidence

ORD record
ord-ad3bc87243ae4ad99ff94476e27b1e04
Source dataset
uspto-grants-1999_02
Patent number
US05869482

Reaction notes

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