Trimethylsilylacetylene → HCID 72212432, compound

HRID 2373210Notes

Reaction equation

HRID 2373210 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:9]=1)[CH:7]=[O:8].[C:10]([Si:12]([CH3:15])([CH3:14])[CH3:13])#[CH:11]>CCN(CC)CC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[CH3:13][Si:12]([C:10]#[C:11][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:9]=1)[CH:7]=[O:8])([CH3:15])[CH3:14]

Participants

6

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 27847345-Bromo-3-pyridinecarboxaldehyde

Product 1

HCID 72212432HCID 72212432, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

To a stirred solution of 5-bromonicotinaldehyde (1 g) and ethynyltrimethylsilane (792 mg) in Et3N (15 ml) was added tetrakis(triphenylphosphine)palladium (124 mg) and copper(I) iodide (51 mg). After 4 hours, the resulting mixture was filtrated and evaporated. The residue was dissolved in EtOAc and washed successively with dil. NH3aq, water and brine. The organic layer was dried over MgSO4 and evaporated. The residue was purified with silica gel column chromatography to give 5-[(trimethylsilyl)ethynyl]nicotinaldehyde as a slightly yellow oil.

Workup

  1. filtrationthe resulting mixture was filtrated
  2. customevaporated
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed successively with dil. NH3aq, water and brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. customevaporated
  7. customThe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-b02b808dbca9444a91d6e7bcac2edc46
Source dataset
uspto-grants-2008_12
Patent number
US07459451B2

Reaction notes

Loading…