4-Pentyn-1-ol → 5-[1-(4-Trimethylsilanylethynyl-phenyl)-1H-indol-5-yl]-pent-4-yn-1-ol

HRID 1633663Notes

Reaction equation

HRID 1633663 reaction equation
[CH3:1][Si:2]([C:5]#[C:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:21]3[C:16](=[CH:17][C:18](OS(C(F)(F)F)(=O)=O)=[CH:19][CH:20]=3)[CH:15]=[CH:14]2)=[CH:9][CH:8]=1)([CH3:4])[CH3:3].[CH2:30]([OH:35])[CH2:31][CH2:32][C:33]#[CH:34]>N1CCCCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu]I>[CH3:3][Si:2]([C:5]#[C:6][C:7]1[CH:8]=[CH:9][C:10]([N:13]2[C:21]3[C:16](=[CH:17][C:18]([C:34]#[C:33][CH2:32][CH2:31][CH2:30][OH:35])=[CH:19][CH:20]=3)[CH:15]=[CH:14]2)=[CH:11][CH:12]=1)([CH3:4])[CH3:1]

Participants

6

Reactant 2

HCID 793464-Pentyn-1-olHCID 86585591Trifluoro-methanesulfonic acid 1-(4-trimethylsilanylethynyl-phenyl)-1H-indol-5-yl ester

Product 1

HCID 186794765-[1-(4-Trimethylsilanylethynyl-phenyl)-1H-indol-5-yl]-pent-4-yn-1-olYield 71.3%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8082PiperidineSolvent

Conditions

Temperature
80 °C

Procedure

To 1.62 g (3.7 mmol) Trifluoro-methanesulfonic acid 1-(4-trimethylsilanylethynyl-phenyl)-1H-indol-5-yl ester in 5 ml piperidine, 230 mg (0.2 mmol) tetrakis-(triphenylphosphine)-palladium and 40 mg (0.2 mmol) CuI were added. The solution was evaporated and purged with argon three times, before 0.56 ml (6 mmol) 4-pentyn-1-ol were added. The solution was stirred at 80° C. for 2 h. The solution was concentrated and the residue dissolved in 0.5M HCl and ether. The inorganic phase was extracted with ether, the organic phases were washed with water and dried over Na2SO4. Purification on silica gel with CH2Cl2 yielded 980 mg (71%) 5-[1-(4-Trimethylsilanylethynyl-phenyl)-1H-indol-5-yl]-pent-4-yn-1-ol as orange viscous oil, MS: 371 (M).

Workup

  1. customThe solution was evaporated
  2. additionwere added
  3. concentrationThe solution was concentrated
  4. dissolutionthe residue dissolved in 0.5M HCl
  5. extractionThe inorganic phase was extracted with ether
  6. washthe organic phases were washed with water
  7. dry with materialdried over Na2SO4
  8. customPurification on silica gel with CH2Cl2

Sources & evidence

ORD record
ord-f7f57941906c4b52887534cd90ccc342
Source dataset
uspto-grants-2003_01
Patent number
US06503907B2

Reaction notes

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