Trimethylsilylacetylene → Trifluoro-methanesulfonic acid 1-(4-trimethylsilanylethynyl-phenyl)-1H-indol-5-yl ester

HRID 1633662Notes

Reaction equation

HRID 1633662 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][S:18]([C:21]([F:24])([F:23])[F:22])(=[O:20])=[O:19])=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[CH:4][CH:3]=1.[C:25]([Si:27]([CH3:30])([CH3:29])[CH3:28])#[CH:26]>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>[CH3:28][Si:27]([C:25]#[C:26][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][S:18]([C:21]([F:23])([F:22])[F:24])(=[O:20])=[O:19])=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[CH:4][CH:3]=1)([CH3:30])[CH3:29]

Participants

6

Reactant 2

HCID 66111Trimethylsilylacetylene2×HCID 86585588HCID 86585588, compound

Product 1

HCID 86585591Trifluoro-methanesulfonic acid 1-(4-trimethylsilanylethynyl-phenyl)-1H-indol-5-yl esterYield 38.9%

Reagents, catalysts & solvents 3

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

Procedure

To 4.2 g (10 mmol) Trifluoro-methanesulfonic acid 1-(4-bromo-phenyl)-1H-indol-5-yl ester in 30 ml piperidine, 580 mg (0.5 mmol) tetrakis-(triphenylphosphine)-palladium and 100 mg (0.625 mmol) CuI were added. The solution was evaporated and purged with argon three times, before 1.4 ml (10 mmol) ethynyltrimethylsilane were added. The solution was stirred at RT for 48 h. Additional 0.38 ml (3.3 mmol) ethynyltrimethylsilane were added and the mixture was stirred at 50° C. for 1 h. The solution was concentrated and the residue redissolved 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 hexane/EtOAc 19:1 yielded 1.7 g (38%) Trifluoro-methanesulfonic acid 1-(4-trimethylsilanylethynyl-phenyl)-1H-indol-5-yl ester as orange oil, MS: 437 (M).

Workup

  1. customThe solution was evaporated
  2. additionwere added
  3. stirringthe mixture was stirred at 50° C. for 1 h
  4. concentrationThe solution was concentrated
  5. dissolutionthe residue redissolved in 0.5M HCl
  6. extractionThe inorganic phase was extracted with ether
  7. washthe organic phases were washed with water
  8. dry with materialdried over Na2SO4
  9. customPurification on silica gel with hexane/EtOAc 19:1

Sources & evidence

ORD record
ord-4ad64b94700f473d822f6d72a7217c2b
Source dataset
uspto-grants-2003_01
Patent number
US06503907B2

Reaction notes

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