Triethylamine → 2,2,2-Trifluoro-1-{5-[(trimethylsilyl)ethynyl]-2-thienyl}ethanone

HRID 1715349Notes

Reaction equation

HRID 1715349 reaction equation
BrC1SC=CC=1.Br[C:8]1[S:12][C:11]([C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=1.CCN(CC)CC.[CH3:26][Si:27]([C:30]#[CH:31])([CH3:29])[CH3:28]>C1COCC1.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>[F:15][C:14]([F:17])([F:16])[C:13]([C:11]1[S:12][C:8]([C:31]#[C:30][Si:27]([CH3:29])([CH3:28])[CH3:26])=[CH:9][CH:10]=1)=[O:18]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 138512-BromothiopheneHCID 66111TrimethylsilylacetyleneHCID 199715871-(5-Bromothiophen-2-yl)-2,2,2-trifluoroethan-1-one

Product 1

HCID 685070782,2,2-Trifluoro-1-{5-[(trimethylsilyl)ethynyl]-2-thienyl}ethanone

Reagents, catalysts & solvents 3

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

Procedure

A mixture of 5-bromo-thiophene Example 3, C2 (1.0 eq), Pd(PPh3)2Cl2 (0.025 eq), CuI (0.05 eq) and Et3N (28.7 eq) in THF (0.25 M) was degassed with a stream of Ar for 30 min. Trimethylsilylacetylene (1.5 eq) was added and the mixture was stirred O/N at RT. Evaporation of the solvent gave a residue which was purified by flash column chromatography on silica using 0-5% EtOAc/Petroleum ether to yield the desired compound as a yellow oil. 1H NMR (300 MHz, CDCl3, 300K) δ 7.83-7.78 (1H, m), 7.25 (1H, bs), 0.28 (9H, s).

Workup

  1. customwas degassed with a stream of Ar for 30 min
  2. customEvaporation of the solvent
  3. customgave a residue which
  4. customwas purified by flash column chromatography on silica using 0-5% EtOAc/Petroleum ether

Sources & evidence

ORD record
ord-31f1ae1c8f914accaf5210aecfa5c8e3
Source dataset
uspto-grants-2010_09
Patent number
US07799825B2

Reaction notes

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