Methyl iodide → 5-(4-Fluoro-3-methoxyphenylethynyl)-nicotinonitrile

HRID 606865Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 606865
[OH:1][C:2]1[CH:3]=[C:4]([C:9]#[C:10][C:11]2[CH:12]=[N:13][CH:14]=[C:15]([CH:18]=2)[C:16]#[N:17])[CH:5]=[CH:6][C:7]=1[F:8].IC.[C:21](=O)([O-])[O-].[K+].[K+]>C(#N)C.C([O-])=O.[Na+]>[F:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]#[C:10][C:11]2[CH:12]=[N:13][CH:14]=[C:15]([CH:18]=2)[C:16]#[N:17])=[CH:3][C:2]=1[O:1][CH3:21]

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 670478145-(3-Hydroxy-4-fluorophenylethynyl)-nicotinonitrile

Produkt 1

HCID 670476015-(4-Fluoro-3-methoxyphenylethynyl)-nicotinonitrileAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 2723810Sodium FormateLösungsmittel

Versuchsvorschrift

Dissolve 5-(3-hydroxy-4-fluorophenylethynyl)-nicotinonitrile, (prepared essentially as described in EXAMPLE 77), (150 mg, 0.63 mmol) in anhydrous acetonitrile (5 mL) and sequentially add iodomethane (59 μL, 0.95 mmol) and potassium carbonate (174 mg, 1.26 mmol). Stir at room temperature for 12 h, dilute with an aqueous saturated solution of sodium carbanate and extract with dichloromethane. Sequentially wash the organic layer with water and an aqueous saturated solution of sodium chloride, dry (magnesium sulfate), filter and concentrate. Purify by silica gel chromatography, eluting with 30:70 ethyl acetate:hexanes, to give the title compound (70 mg, 44%) as white solid.

Aufarbeitung

  1. custom(prepared essentially
  2. extractionextract with dichloromethane
  3. washSequentially wash the organic layer with water
  4. dry with materialan aqueous saturated solution of sodium chloride, dry (magnesium sulfate)
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify by silica gel chromatography
  8. washeluting with 30:70 ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-6df40998fc094812bd0c24e197d446db
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915424B2

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