Trimethylsilylacetylene → HCID 69349409, Verbindung

HRID 1948279Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1948279
I[C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[CH:12]=[CH:11][C:10]2=[O:23])=[CH:4][CH:3]=1.C(N(C(C)C)C(C)C)C.[CH3:33][Si:34]([C:37]#[CH:38])([CH3:36])[CH3:35]>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.[Cu]I.CN(C=O)C>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([C:13]2[CH:12]=[CH:11][C:10](=[O:23])[N:9]([CH2:8][C:5]3[CH:6]=[N:7][C:2]([C:38]#[C:37][Si:34]([CH3:36])([CH3:35])[CH3:33])=[CH:3][CH:4]=3)[CH:14]=2)=[CH:16][CH:17]=1

Komponenten

7

Edukt 3

HCID 66111TrimethylsilylacetyleneHCID 81531DiisopropylethylamineHCID 862293681-((6-Iodopyridin-3-yl)methyl)-5-(4-methoxyphenyl)pyridin-2(1H)-one

Produkt 1

HCID 69349409HCID 69349409, VerbindungAusbeute 93,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

According to Scheme 33 Step 2: A mixture of 1-((6-iodopyridin-3-yl)methyl)-5-(4-methoxyphenyl)pyridin-2(1H)-one (0.48 mmol, 200 mg), PdCl2(PPh3)2 (33 μmol, 23 mg), CuI (24 μmol, 4.5 mg), iPr2EtN (0.99 mmol, 1.72 μl), trimethylsilylacetylene (1.43 mmol, 203 μL) and DMF (3 mL, previously deoxygenated) was stirred at room temperature for 2 hours. The solvent was evaporated under reduced pressure. The residue was purified in a manifold (vac.) using a Sep-Pak silica cartridge CH2Cl2/MeOH(NH3)sat. 3% yielding 5-(4-methoxyphenyl)-1-((6-(2-(trimethylsilyl)ethynyl)pyridin-3-yl)methyl)pyridin-2(1H)-one (174 mg, 93%).

Aufarbeitung

  1. custompreviously deoxygenated)
  2. customThe solvent was evaporated under reduced pressure
  3. customThe residue was purified in a manifold (vac.)

Quellen und Nachweise

ORD-Eintrag
ord-9fd1087fd58947469aeda82205facf51
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399493B2

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