Phenylacetylene → HCID 67047572, compound

HRID 606842Notes

Reaction equation

HRID 606842 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]([O:16][CH3:17])[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>[CH3:17][O: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 8171633-Bromo-5-methoxypyridine

Product 1

HCID 67047572HCID 67047572, compoundYield 66%

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 (0.180 mL, 1.6 mmol), copper (I) iodide (0.029 g, 0.15 mmol) and bis(triphenylphosphine)palladium (II) dichloride (0.053 g, 0.08 mmol) to a solution of 3-bromo-5-methoxypyridine (0.282 g, 1.5 mmol) in degassed triethylamine (8 mL) and heat 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 50:50 to 0:100 hexanes:ethyl acetate to give the title compound (0.206 g, 66%).

Workup

  1. temperatureCool the reaction mixture 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 50:50 to 0:100 hexanes

Sources & evidence

ORD record
ord-12e6e00e79b4416fb80b6826b2c3c8e9
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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