2-bromo-3-trifluoromethylpyridine → HCID 71563079, compound

HRID 1844391Notes

Reaction equation

HRID 1844391 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1)#[CH:2].Br[C:14]1[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:17]=[CH:16][N:15]=1.CCOC(C)=O.CCCCCC>C(N(CC)CC)C.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:21][C:20]([F:23])([F:22])[C:19]1[C:14]([C:2]#[C:1][C:3]2[CH:12]=[CH:11][C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[N:4]=2)=[N:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 3

HCID 51938202-bromo-3-trifluoromethylpyridineHCID 130817492-EthynylquinolineHCID 21226206Ethyl acetate hexane

Product 1

HCID 71563079HCID 71563079, compound

Reagents, catalysts & solvents 3

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

Conditions

Temperature
85 °C

Procedure

To the solution in which 2-ethynylquinoline (50 mg, 0.33 mmol) was dissolved in triethylamine (0.4 mL), PdCl2(PPh3)2 (12 mg, 0.02 mmol), CuI (6 mg, 0.03 mmol), and 2-bromo-3-trifluoromethylpyridine (110 mg, 0.5 mmol) were added, followed by stirring at 85° C. for 3 hr. The completion of the reaction was confirmed by TLC (EtOAc/Hexane=1:1). The reactant was cooled down to room temperature and filtered through Celite. The thus obtained filtrate was extracted with EtOAc (3×10 mL), to thereby obtain an organic layer. The organic layer was washed with a saturated aqueous solution of NaCl. The organic layer was then dried over anhydrous MgSO4, concentrated under reduced pressure, and purified by column chromatography (EtOAc/hexane=1:1), to thereby obtain 2-((3-(trifluoromethyl)pyridine-2-yl)ethynyl)quinoline (48 mg, 49%) as a brown solid.

Workup

  1. temperatureThe reactant was cooled down to room temperature
  2. filtrationfiltered through Celite
  3. extractionThe thus obtained filtrate was extracted with EtOAc (3×10 mL)
  4. customto thereby obtain an organic layer
  5. washThe organic layer was washed with a saturated aqueous solution of NaCl
  6. dry with materialThe organic layer was then dried over anhydrous MgSO4
  7. concentrationconcentrated under reduced pressure
  8. custompurified by column chromatography (EtOAc/hexane=1:1)

Sources & evidence

ORD record
ord-083853fcf75f4f15b5da9298c7035f59
Source dataset
uspto-grants-2015_02
Patent number
US08946431B2

Reaction notes

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