Phenylacetylene → 3-Phenylethynyl-pyridine

HRID 606830Notes

Reaction equation

HRID 606830 reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1>C(N(CC)CC)C.[Cu]I.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]1([C:7]#[C:8][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 2

HCID 10821PhenylacetyleneHCID 122863-Bromopyridine

Product 1

HCID 109430453-Phenylethynyl-pyridineYield 35.1%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178419050HCID 178419050, compoundCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
80 °C

Procedure

Add phenylacetylene (0.175 mL, 1.6 mmol), copper (I) iodide (0.028 g, 0.15 mmol) and bis(triphenylphosphine)palladium (II) dichloride (0.051 g, 0.07 mmol) to a solution of 3-bromopyridine (0.140 mL, 1.45 mmol) in degassed triethylamine (6 mL) and stir under nitrogen at 80° C. for 16 h. Cool to room temperature, filter through diatomaceous earth, wash with ethyl acetate, and concentrate. Purify the residue by silica gel chromatography, eluting with 100:0 to 0:100 hexanes:dichlormethane, to give the title compound (91.1 mg, 35%).

Workup

  1. temperatureCool to room temperature
  2. filtrationfilter through diatomaceous earth
  3. washwash with ethyl acetate
  4. concentrationconcentrate
  5. customPurify the residue by silica gel chromatography
  6. washeluting with 100:0 to 0:100 hexanes

Sources & evidence

ORD record
ord-f093eddfdd414106971a3bb01a6ec04d
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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