Triethylamine → 2-(Phenylethynyl)quinoline

HRID 1844389Notes

Reaction equation

HRID 1844389 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.C(N(CC)CC)C.[C:19]1([C:25]#[CH:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CCOC(C)=O.CCCCCC>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>[C:19]1([C:25]#[C:26][C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 119282-ChloroquinolineHCID 21226206Ethyl acetate hexane

Product 1

HCID 126695772-(Phenylethynyl)quinoline

Reagents, catalysts & solvents 3

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

Procedure

After 2-chloroquinoline (29.7 mg, 0.182 mmole) was dissolved in THF (1.5 mL), PdCl2(PPh3)2 (2.6 mg, 0.0037 mmole), and CuI (1.5 mg, 0.0063 mmol) were added thereto and stirred for 5 min under nitrogen atmosphere. To the resulting mixture triethylamine (0.15 mL) and phenylacetylene (0.03 mL, 0.273 mmol) were successively added, followed by stirring at 80° C. for 24 hr after sealing. The completion of the reaction was confirmed by TLC (EtOAc/Hexane=1:10). When the reaction was completed, the reactant was filtered through Celite and extracted with a mixture of EtOAc and H2O, to thereby separate an organic layer. The organic layer was dried over anhydrous MgSO4, concentrated under reduced pressure, and purified by column chromatography (EtOAc/Hexane=1:10, R.f: 0.35), to thereby obtain 2-(phenylethynyl)quinoline (24.9 mg, 60%) as a brown solid.

Workup

  1. stirringby stirring at 80° C. for 24 hr after sealing
  2. filtrationthe reactant was filtered through Celite
  3. extractionextracted with a mixture of EtOAc and H2O
  4. customto thereby separate an organic layer
  5. dry with materialThe organic layer was dried over anhydrous MgSO4
  6. concentrationconcentrated under reduced pressure
  7. custompurified by column chromatography (EtOAc/Hexane=1:10, R.f: 0.35)

Sources & evidence

ORD record
ord-b7d6ef74f98045c5842e938ba425bd79
Source dataset
uspto-grants-2015_02
Patent number
US08946431B2

Reaction notes

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