3-(3-Formyl-pyridin-4-yl)-benzonitrile → 3-{3-[(3-Fluoro-4-methoxy-phenyl)-hydroxy-methyl]-pyridin-4-yl)-benzonitrile

HRID 1712091Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1712091
[CH:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[C:12]#[N:13])=[O:2].[F:17][C:18]1[CH:19]=[C:20]([Mg]Br)[CH:21]=[CH:22][C:23]=1[O:24][CH3:25]>C1COCC1>[F:17][C:18]1[CH:19]=[C:20]([CH:1]([OH:2])[C:3]2[CH:4]=[N:5][CH:6]=[CH:7][C:8]=2[C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[C:12]#[N:13])[CH:21]=[CH:22][C:23]=1[O:24][CH3:25]

Komponenten

4

Edukt 2

HCID 592052083-(3-Formyl-pyridin-4-yl)-benzonitrileHCID 178491915HCID 178491915, Verbindung

Produkt 1

HCID 592051783-{3-[(3-Fluoro-4-methoxy-phenyl)-hydroxy-methyl]-pyridin-4-yl)-benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 3-(3-formyl-pyridin-4-yl)-benzonitrile (15 mg, 0.075 mmol) in THF (1 mL) at −78° C. was added 0.5 M 3-fluoro-4-methoxyphenylmagnesium bromide in THF (0.3 mL). The reaction mixture was quenched with ammonium chloride and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, concentrated, and the residue purified by flash chromatography eluted with 5% methanol in dichloromethane to yield 3-{3-[(3-fluoro-4-methoxy-phenyl)-hydroxy-methyl]-pyridin-4-yl}-benzonitrile as a colorless oil.

Aufarbeitung

  1. customThe reaction mixture was quenched with ammonium chloride
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. customthe residue purified by flash chromatography
  6. washeluted with 5% methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-a67c2c4da0dc4b32a2c3aee617ab79bf
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790895B2

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