Triethylamine → 4-(Phenylethynyl)pyridine

HRID 271110Notes

Reaction equation

HRID 271110 reaction equation
Cl.Br[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:16]1([C:22]#[CH:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:16]1([C:22]#[C:23][C:3]2[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 881004-Bromopyridinium chloride

Product 1

HCID 3521724-(Phenylethynyl)pyridineYield 91%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 4-bromopyridine hydrochloride (3.9 g, 20 mmol), tetrakis(triphenylphosphine)palladium (2.32 g, 2.0 mmol), triethylamine (16.8 mL, 120 mmol) in dry DMF (150 mL) is added phenylacetylene (4.2 mL, 40 mmol) at room temperature. After stirring for 3 hours at 80° C., the reaction mixture is concentrated. The residue is dissolved in CH2Cl2 (100 mL), washed with H2O, brine (50 mL), dried (MgSO4) and concentrated. The crude material is purified by chromatography (silica gel, EtOAc/hexane: 10/90) to afford the title compound as a solid (3.25 g, 91%). Mp 51-53° C. MS (+) ES: 180 (M+H)+.

Workup

  1. concentrationthe reaction mixture is concentrated
  2. dissolutionThe residue is dissolved in CH2Cl2 (100 mL)
  3. washwashed with H2O, brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe crude material is purified by chromatography (silica gel, EtOAc/hexane: 10/90)

Sources & evidence

ORD record
ord-9aaebb51c18c4dbfa6675e1f33750886
Source dataset
uspto-grants-2008_11
Patent number
US07452885B2

Reaction notes

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