Phenylacetylene → 3-Methyl-5-phenylethynylpyridine

HRID 606828Notes

Reaction equation

HRID 606828 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]=[C:14]([CH3:16])[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>[CH3:16][C:14]1[CH:13]=[N:12][CH:11]=[C:10]([C:8]#[C:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:15]=1

Participants

6

Reactant 2

HCID 10821PhenylacetyleneHCID 8177133-Bromo-5-methylpyridine

Product 1

HCID 670477253-Methyl-5-phenylethynylpyridineYield 54%

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 (0.460 mL, 4.2 mmol), copper (I) iodide (0.072 g, 0.38 mmol) and bis(triphenylphosphine)palladium (II) dichloride (0.133 g, 0.19 mmol) to a solution of 3-bromo-5-methylpyridine, (prepared essentially as described in PREPARATION 1), (0.654 g, 3.8 mmol) in degassed triethylamine (20 mL) and stir under nitrogen at 80° C. for 16 h. Cool the reaction mixture to room temperature, filter through diatomaceous earth, wash with ethyl acetate, and concentrate. Purify the residue by silica gel chromatography, eluting with 80:20 hexanes:ethyl acetate, to give the title compound as a brown oil (0.398 g, 54%).

Workup

  1. custom(prepared essentially
  2. temperatureCool the reaction mixture to room temperature
  3. filtrationfilter through diatomaceous earth
  4. washwash with ethyl acetate
  5. concentrationconcentrate
  6. customPurify the residue by silica gel chromatography
  7. washeluting with 80:20 hexanes

Sources & evidence

ORD record
ord-b375ee4b7c78418b8fb43080b1f122e3
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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