Cesium carbonate → 9-Fluoro-6-phenanthridinamine

HRID 338189

Reaktionsgleichung

Reaktionsgleichung von HRID 338189
Cl[C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1B1OC(C)(C)C(C)(C)O1.C1C2CC3(N)CC(C2)CC1C3.Cl.C(=O)([O-])[O-].[Cs+].[Cs+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(Cl)Cl.O.O1CCOCC1>[F:10][C:8]1[CH:7]=[CH:6][C:3]2[C:2]([CH:9]=1)=[C:13]1[C:12]([CH:17]=[CH:16][CH:15]=[CH:14]1)=[N:11][C:4]=2[NH2:5]

Komponenten

9

Edukt 4

HCID 10796Cesium carbonateHCID 64150Amantadine HydrochlorideHCID 1090002-Chloro-4-fluorobenzonitrileHCID 27346522-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Produkt 1

HCID 112528289-Fluoro-6-phenanthridinamineAusbeute 3.082,6 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 2-chloro-4-fluorobenzonitrile (1.0 g, 6.42 mmol), 2-aminophenylboronic acid pinacol ester (1.6 g, 7.1 mmol), palladium(II) acetate (0.07 g, 0.32 mmol), amantadine hydrochloride (0.24 g, 1.3 mmol) and cesium carbonate (4.6 g, 14.1 mmol) were added to dioxane previously deaerated with nitrogen and heated to reflux for 17 hours. After cooling, both distilled water and methylene chloride (50 mL) were added to the reaction mixture. The solvent layer was separated and concentrated to give a crude oil that was purified by column chromatography by first using 1:1 ethyl acetate and hexanes ratio followed by 4:1 ethyl acetate/hexanes as the eluants. The pure product was collected to give 9-fluoro-6-phenanthridinamine (42 g, 32% Yield) whose NMR spectrum is consistent with the proposed structure.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 17 hours
  3. temperatureAfter cooling
  4. customThe solvent layer was separated
  5. concentrationconcentrated
  6. customto give a crude oil that
  7. customwas purified by column chromatography
  8. customThe pure product was collected

Quellen und Nachweise

ORD-Eintrag
ord-f33504768f854612ad3dd57118648f0e
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889864B2

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