Trimethylsilylacetylene → HCID 178434278, compound

HRID 598869Notes

Reaction equation

HRID 598869 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[CH3:11].[C:12]([Si:14]([CH3:17])([CH3:16])[CH3:15])#[CH:13]>CCN(CC)CC.[Cu]I>[CH3:11][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([C:13]#[C:12][Si:14]([CH3:17])([CH3:16])[CH3:15])[CH:3]=2)[NH:7][N:6]=1

Participants

5

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 178434225HCID 178434225, compound

Product 1

HCID 178434278HCID 178434278, compound

Reagents, catalysts & solvents 2

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

Procedure

5-Bromo-3-methyl-1H-indazole (1.72 g, 8.2 mmol), PdCl2(PPh)2 (1.14 g, 1.64 mmol), CuI (155 mg, 0.82 mmol) and ethynyltrimethylsilane (3.5 mL, 24.6 mmol) were dissolved in 180 mL Et3N and refluxed over night. The mixture was cooled to room temperature, filtered and evaporated. The residue was taken up in MeOH (100 mL), filtered again and evaporated. The product thus obtained was purified on glass column chromatography (20% EtOAc in hexane). The title compound was obtained as a dark solid. LCMS (API-ES) m/z (%): 229.0 (100%, M++H).

Workup

  1. temperaturerefluxed over night
  2. filtrationfiltered
  3. customevaporated
  4. filtrationfiltered again
  5. customevaporated
  6. customThe product thus obtained
  7. customwas purified on glass column chromatography (20% EtOAc in hexane)

Sources & evidence

ORD record
ord-a94f8a83202244e9a91024c1dc8aae21
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Reaction notes

Loading…