1-Ethynyl-4-methoxybenzene → 4-[2-(4-Methoxyphenyl)ethynyl]pyridine

HRID 33929

Reaction equation

HRID 33929 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[CH:10])=[CH:5][CH:4]=1.I[C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1>O1CCCC1.C(N(CC)CC)C.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>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 2

HCID 2510201-Ethynyl-4-methoxybenzeneHCID 6094924-Iodopyridine

Product 1

HCID 45952534-[2-(4-Methoxyphenyl)ethynyl]pyridine

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 4-methoxyphenylacetylene (2.86 g, 21.7 mmol), 4-iodopyridine (4.44 g, 21.7 mmol), cuprous iodide (206 mg, 1.08 mmol), bis(triphenylphosphine)palladium(II) dichloride (758 mg, 1.08 mmol) in tetrahydrofuran (40 mL) and triethylamine (20 mL) was heated at reflux for 2 h. The mixture was filtered, concentrated, and the residue chromaptographed on silica in 1:1 ethyl acetate-hexanes giving 2.45 g (54%) of a yellow solid. 1H NMR (CDCl3, 400 mHz) δ 9.2 (very broad, 2H), 7.57 (br, 2H), 7.48 (d, 2H, J=8.7 Hz), 6.88 (d, 2H, J=8.7 Hz), 3.82 (s, 3H). MS (AP+) m/e 210 (MH+).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a91595138b5f488cacc2de9fb51cb49d
Source dataset
uspto-grants-2008_09
Patent number
US07429665B2

Linked notes

Loading…