Potassium Carbonate → 2-Furan-3-yl-6-methoxy-1H-indole

HRID 2409958Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2409958
FC(F)(F)C([NH:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:7]=1I)=O.[O:17]1[CH:21]=[CH:20][C:19]([C:22]#[C:23][Si](C)(C)C)=[CH:18]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>[O:17]1[CH:21]=[CH:20][C:19]([C:22]2[NH:5][C:6]3[C:7]([CH:23]=2)=[CH:8][CH:9]=[C:10]([O:12][CH3:13])[CH:11]=3)=[CH:18]1

Komponenten

11

Edukt 4

HCID 11430Potassium CarbonateHCID 2724141Tetrabutylammonium FluorideHCID 16217672[2-(Furan-3-yl)ethynyl]trimethylsilaneHCID 221434932,2,2-Trifluoro-N-(2-iodo-5-methoxy-phenyl)-acetamide

Produkt 1

HCID 867032792-Furan-3-yl-6-methoxy-1H-indoleAusbeute 68,3 %

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), furan-3-ylethynyltrimethylsilane (714 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 (422 mg). 1H-NMR (CDCl3) δ ppm: 3.86 (3H, s), 6.51-6.56 (1H, m), 6.64-6.69 (1H, m), 6.78 (1H, dd, J=2.3, 8.5 Hz), 6.84-6.90 (1H, m), 7.42-7.51 (2H, m), 7.67-7.73 (1H, m), 7.78-8.13 (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-7f70ba1d5b3742818b70528496818d22
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08815903B2

Notizen zur Reaktion

Wird geladen…