Dimethylformamide → 2-Fluoro-4-(5-fluoro-pyridin-2-ylmethoxy)benzaldehyde

HRID 78078

Reaktionsgleichung

Reaktionsgleichung von HRID 78078
CN(C)C=O.[F:6][C:7]1[CH:14]=[C:13]([OH:15])[CH:12]=[CH:11][C:8]=1[CH:9]=[O:10].[H-].[Na+].Cl[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][N:21]=1>O>[F:6][C:7]1[CH:14]=[C:13]([O:15][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][N:21]=2)[CH:12]=[CH:11][C:8]=1[CH:9]=[O:10]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 5872462-Fluoro-4-hydroxybenzaldehydeHCID 216980592-(Chloromethyl)-5-fluoropyridine

Produkt 1

HCID 592553562-Fluoro-4-(5-fluoro-pyridin-2-ylmethoxy)benzaldehydeAusbeute 42,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To an N,N-dimethylformamide (20.0 mL) solution of 2-fluoro-4-hydroxy-benzaldehyde (1.48 g, 10.2 mmol) was added sodium hydride (411 mg, 10.3 mmol, 60% in oil) under nitrogen atmosphere at 0° C., which was stirred for 20 minutes at room temperature. 2-Chloromethyl-5-fluoro-pyridine (1.20 g, 8.56 mmol) described in Manufacturing Example 41-1-2 was then added at room temperature, and stirred for 30 minutes at 80° C. Water was added at room temperature to the reaction solution, which was then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, and the solvent was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate: heptane=1:5→1:2) to obtain the title compound (901 mg, 42.2%).

Aufarbeitung

  1. additionwas then added at room temperature
  2. stirringstirred for 30 minutes at 80° C
  3. extractionwas then extracted with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous sodium chloride
  5. customthe solvent was evaporated under a reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate: heptane=1:5→1:2)

Quellen und Nachweise

ORD-Eintrag
ord-e59ad0926dcc4ad1bd33fd2bc9387c76
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841327B2

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