Isopropanol → (5-(2-(dimethylamino)ethoxy)pyridin-2-yl)(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)methanone

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Reaktionsgleichung

I[C:2]1[CH:14]=[CH:13][C:5]([O:6][CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][O:8]2)=[CH:4][CH:3]=1.CCCCCC.[CH3:21][N:22]([CH3:38])[CH2:23][CH2:24][O:25][C:26]1[CH:27]=[CH:28][C:29]([C:32](N(OC)C)=[O:33])=[N:30][CH:31]=1.C(O)(C)C>C1COCC1.O>[CH3:21][N:22]([CH3:38])[CH2:23][CH2:24][O:25][C:26]1[CH:27]=[CH:28][C:29]([C:32]([C:2]2[CH:14]=[CH:13][C:5]([O:6][CH:7]3[CH2:12][CH2:11][CH2:10][CH2:9][O:8]3)=[CH:4][CH:3]=2)=[O:33])=[N:30][CH:31]=1

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

To a solution of 2-(4-iodophenoxy)tetrahydro-2H-pyran (1.1 eq) in THF was added a solution of nbutyllitium in hexane (1.1 eq) at −78° C. The mixture was stirred at −78° C. for 20 min. To the mixture was added a solution of 5-(2-(dimethylamino)-ethoxy)-N-methoxy-N-methylpicolinamide (1.0 eq) in THF at −78° C. After 2 h, isopropanol and water was added to the mixture, and the cold bath was removed. The mixture was stirred at room temperature for 20 min. The mixture was extracted with ethyl acetate. The extract was washed with 0.5 N HCl, sodium bicarbonate (sat.), and brine, dried over sodium sulfate, filtered, concentrated, and purified by column chromatography (silica gel) to give the subtitle compound (47% yield).

Aufarbeitung

waitAfter 2 h
customthe cold bath was removed
stirringThe mixture was stirred at room temperature for 20 min
extractionThe mixture was extracted with ethyl acetate
washThe extract was washed with 0.5 N HCl, sodium bicarbonate (sat.), and brine
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated
custompurified by column chromatography (silica gel)

Quellen und Nachweise

ORD-Eintrag: ord-51921f24e10b479c950a043a97582218
Quelldatensatz: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09309211B2

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