2-Iodopyridine → 2-(6-(4-Fluorophenyl)hexa-1,5-diynyl)pyridine

HRID 1189083Notes

Reaction equation

HRID 1189083 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[F:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[C:16][CH2:17][CH2:18][C:19]#[CH:20])=[CH:11][CH:10]=1>C(N(CC)CC)C.[Cu](I)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>[F:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[C:16][CH2:17][CH2:18][C:19]#[C:20][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:11][CH:10]=1

Participants

6

Reactant 2

HCID 2211262-IodopyridineHCID 860867911-Fluoro-4-(hexa-1,5-diynyl)benzene

Product 1

HCID 115578602-(6-(4-Fluorophenyl)hexa-1,5-diynyl)pyridineYield 29.1%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent2×

Procedure

In a dry reaction tube containing in suspension copper iodide (11 mg, 0.06 mmol) and triethylamine (3.4 mL), were added 2-iodopyridine (246 mg, 1.2 mmol) and Pd(PPh3)2Cl2 (42 mg, 0.06 mmol) under N2. A yellow suspension was obtained after 5 min of stirring at room temperature. A solution of 1-fluoro-4-(hexa-1,5-diynyl)benzene (210 mg, 1.2 mmol) in triethylamine (0.5 mL) was then added under N2. Immediately the color of the reaction turns to black. The mixture was stirred at room temperature for 48h. The reaction mixture was concentrated. The crude product was dissolved in DCM and the organic phase was washed with saturated NH4Cl, water and brine. The organic layer was dried over MgSO4, filtered, and concentrated. Purification by Flash chromatography (prepacked 25 g silicagel column, Cyclohexane/ethyl acetate from 90/10to 80/20 as eluent) to afford 87 mg of 2-(6-(4-fluorophenyl)hexa-1,5-diynyl)pyridine (Yield: 29%) as a brown powder (M.P.=68-69° C.).

Workup

  1. customIn a dry reaction tube
  2. customA yellow suspension was obtained after 5 min
  3. stirringThe mixture was stirred at room temperature for 48h
  4. concentrationThe reaction mixture was concentrated
  5. dissolutionThe crude product was dissolved in DCM
  6. washthe organic phase was washed with saturated NH4Cl, water and brine
  7. dry with materialThe organic layer was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by Flash chromatography (prepacked 25 g silicagel column, Cyclohexane/ethyl acetate from 90/10to 80/20 as eluent)

Sources & evidence

ORD record
ord-53e251a90b3740718722a94dcb1453a5
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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