Trimethylsilylacetylene → HCID 59164393, compound

HRID 643495Notes

Reaction equation

HRID 643495 reaction equation
I[C:2]1[C:7]([CH:8]=[O:9])=[CH:6][N:5]=[C:4]([O:10][CH3:11])[CH:3]=1.[CH3:12][Si:13]([C:16]#[CH:17])([CH3:15])[CH3:14]>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.[Cu]I.C1COCC1>[CH3:11][O:10][C:4]1[CH:3]=[C:2]([C:17]#[C:16][Si:13]([CH3:15])([CH3:14])[CH3:12])[C:7]([CH:8]=[O:9])=[CH:6][N:5]=1

Participants

6

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 454803254-Iodo-6-methoxynicotinaldehyde

Product 1

HCID 59164393HCID 59164393, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-Iodo-6-methoxynicotinaldehyde (0.41 g, 1.6 mmol), trimethylsilylacetylene (0.35 mL, 2.8 mmol), PdCl2(PPh3)2 (catalytic amount), CuI (catalytic amount), TEA (2 mL) and THF (10 mL) were stirred at 60° C. for 2 h. The volatiles were evaporated and the residue was taken up in water and extracted with ether. The organic phase was dried, filtered and concentrated. Purification by column chromatography with EtOAc-heptanes (1:3) as eluent gave 0.25 g (68% yield) of 6-methoxy-4-[(trimethylsilyl)ethynyl]nicotinaldehyde.

Workup

  1. customThe volatiles were evaporated
  2. extractionextracted with ether
  3. customThe organic phase was dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by column chromatography with EtOAc-heptanes (1:3) as eluent

Sources & evidence

ORD record
ord-5e87fe1c927a4ea7b096a30a5d16f537
Source dataset
uspto-grants-2010_04
Patent number
US07700604B2

Reaction notes

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