2-Chloroquinoline → 2-((Trimethylsilyl)ethynyl)quinoline

HRID 1844387Notes

Reaction equation

HRID 1844387 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:12][Si:13]([C:16]#[CH:17])([CH3:15])[CH3:14].CCOC(C)=O.CCCCCC>C(N(CC)CC)C.[Cu]I.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>[CH3:12][Si:13]([C:16]#[C:17][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1)([CH3:15])[CH3:14]

Participants

7

Reactant 3

HCID 119282-ChloroquinolineHCID 66111TrimethylsilylacetyleneHCID 21226206Ethyl acetate hexane

Product 1

HCID 5133862-((Trimethylsilyl)ethynyl)quinoline

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

2-Chloroquinoline (1.02 g, 6.17 mmol), CuI (12.1 mg, 0.622 mmol), and PdCl2(PPh3)2 (22.7 mg, 0.0317 mmol) were dissolved in triethylamine (20.6 mL), followed by stirring for 5 min. To the resulting mixture, trimethylsilyl acetylene (1.34 mL, 9.44 mmol) was added dropwise at 60° C., followed by heating. The completion of the reaction was confirmed by TLC (EtOAc/Hexane=1:10). When the reaction was completed, the reactant was cooled down to room temperature and extracted with a saturated aqueous solution of NaCl and ethyl acetate, to thereby separate an organic layer. The organic layer was dried over anhydrous MgSO4 and filtered. The filtrate was concentrated under reduced pressure and purified by column chromatography (EtOAc/Hexane=1:10, R.f: 0.4), to thereby obtain 2-((trimethylsilyl)ethynyl)quinoline (1.289 g, 93%) as brown oil.

Workup

  1. temperatureby heating
  2. extractionextracted with a saturated aqueous solution of NaCl and ethyl acetate
  3. customto thereby separate an organic layer
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. custompurified by column chromatography (EtOAc/Hexane=1:10, R.f: 0.4)

Sources & evidence

ORD record
ord-bd8d28cf77fd4fb9bc89f0ac843c4ae9
Source dataset
uspto-grants-2015_02
Patent number
US08946431B2

Reaction notes

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