Dimethylformamide → 4-(3-Fluoro-pyridin-2-yloxymethyl)-benzaldehyde

HRID 1691254

Reaktionsgleichung

[O:1]1CCC[CH2:2]1.Br[C:7]1[CH:21]=[CH:20][C:10]([CH2:11][O:12][C:13]2[C:18]([F:19])=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:9][CH:8]=1.C([Li])CCC.CN(C)C=O>O>[F:19][C:18]1[C:13]([O:12][CH2:11][C:10]2[CH:20]=[CH:21][C:7]([CH:2]=[O:1])=[CH:8][CH:9]=2)=[N:14][CH:15]=[CH:16][CH:17]=1

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

To a tetrahydrofuran (40 mL) solution of 2-(4-bromo-benzyloxy)-3-fluoro-pyridine (2.03 g, 7.20 mmol) described in Manufacturing Example 149-1-1 was added n-Butyl lithium (5.04 mL, 1.6 M hexane solution, 7.92 mmol) under nitrogen atmosphere at −78° C., which was stirred for 45 minutes at −78° C. Then, N,N-dimethylformamide (725 μL, 9.36 mmol) was added to the reaction mixture at −78° C., which was stirred for 1 hour and 10 minutes while the temperature was raised to room temperature. Water was added to the reaction solution at room temperature, which was extracted with ethyl acetate. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=2:1) to obtain the title compound (887 mg, 53%).

Aufarbeitung

stirringwhich was stirred for 1 hour and 10 minutes while the temperature
temperaturewas raised to room temperature
extractionwhich was extracted with ethyl acetate
customThe organic layer was separated
washwashed with saturated aqueous sodium chloride
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
customThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=2:1)

Quellen und Nachweise

ORD-Eintrag: ord-feaa763558e74b04bf22f9921aca196e
Quelldatensatz: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08153662B2

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