Reaktion #1584568

Reaktionsgleichung

1-(2-cyclopropyl-3-methyl-2H-indazol-5-yl)-4-hydroxypyridin-2(1H)-one

(5-bromopyridin-2-yl)methanol

triphenylphosphine

water

→

title compound

Ausbeute 42.4%

4-[(5-bromopyridin-2-yl)methoxy]-1-(2-cyclopropyl-3-methyl-2H-indazol-5-yl)pyridin-2(1H)-one

Ausbeute 42.4%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe mixture was extracted with ethyl acetate
2. 2
   WaschenThe organic layer was washed with saturated brine
3. 3
   Trocknendried over anhydrous magnesium sulfate
4. 4
   Einengenconcentrated under reduced pressure
5. 5
   SonstigeThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate/methanol)
6. 6
   Sonstigerecrystallized from ethanol-hexane

Vorschrift

To a suspension of 1-(2-cyclopropyl-3-methyl-2H-indazol-5-yl)-4-hydroxypyridin-2(1H)-one (50 mg), (5-bromopyridin-2-yl)methanol (67 mg) and triphenylphosphine (140 mg) in tetrahydrofuran (6 ml) was added bis(2-methoxyethyl)azodicarboxylate (125 mg) at room temperature, and the mixture was stirred at the same temperature for 3 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate/methanol) and recrystallized from ethanol-hexane to give the title compound (34 mg).

Quelle