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

HRID 33929

反応式

HRID 33929 の反応式
[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

参加物

6

反応物 2

HCID 2510201-Ethynyl-4-methoxybenzeneHCID 6094924-Iodopyridine

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 8028Tetrahydrofuran溶媒HCID 8471Triethylamine溶媒

実験手順

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+).

後処理

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

出典と根拠

ORDレコード
ord-a91595138b5f488cacc2de9fb51cb49d
出典データセット
uspto-grants-2008_09
特許番号
US07429665B2

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