Potassium Carbonate → 6-Methoxy-2-(5-methylthiophen-3-yl)-1H-indole

HRID 2409956Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2409956
F[C:2](F)(F)[C:3]([NH:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:7]=1I)=O.C[Si](C)(C)C#C[C:21]1[CH:25]=[C:24]([CH3:26])[S:23][CH:22]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.[Cl-].[Na+].O.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu]I.C(#N)C.C(N(CC)CC)C>[CH3:13][O:12][C:10]1[CH:11]=[C:6]2[C:7]([CH:2]=[C:3]([C:21]3[CH:25]=[C:24]([CH3:26])[S:23][CH:22]=3)[NH:5]2)=[CH:8][CH:9]=1

Komponenten

11

Edukt 4

HCID 11430Potassium CarbonateHCID 2724141Tetrabutylammonium FluorideHCID 221434932,2,2-Trifluoro-N-(2-iodo-5-methoxy-phenyl)-acetamideHCID 86703276Trimethyl(5-methylthiophen-3-ylethynyl)silane

Produkt 1

HCID 867032776-Methoxy-2-(5-methylthiophen-3-yl)-1H-indoleAusbeute 63,7 %

Reagenzien, Katalysatoren, Lösungsmittel 6

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysatorHCID 6342AcetonitrileLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a mixture of 2,2,2-trifluoro-N-(2-iodo-5-methoxyphenyl)acetamide (1.00 g), trimethyl(5-methylthiophen-3-ylethynyl)silane (845 mg), bis(triphenylphosphine) palladium(II) dichloride (61 mg), copper(I) iodide (33 mg), triethylamine (0.81 mL), and acetonitrile (15 mL) was added tetrabutylammonium fluoride in tetrahydrofuran solution (1 mol/L, 4.4 mL) at 50° C. This mixture was stirred at 50° C. for 1 hour. Then, potassium carbonate (801 mg) was added thereto, followed by stirring at 50° C. overnight. To the reaction mixture was added saturated brine, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (449 mg). 1H-NMR (CDCl3) δ ppm: 2.53 (3H, d, J=1.0 Hz), 3.86 (3H, s), 6.53-6.59 (1H, m), 6.77 (1H, dd, J=2.3, 8.6 Hz), 6.84-6.89 (1H, m), 7.01-7.11 (2H, m), 7.46 (1H, d, J=8.6 Hz), 7.94-8.16 (1H, br).

Aufarbeitung

  1. stirringby stirring at 50° C. overnight
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-4094b8e81a804684b69062bf461ebb0f
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08815903B2

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