Reaktion #157794

Reaktionsgleichung

1-(Bromomethyl)-4-(methylsulfonyl)benzene

trimethylsilyl chloride

1,2-dibromoethane

tri(2-furyl)phosphine

6-[(Z)-1-bromo-2-(tetrahydro-2H-pyran-4-yl)ethenyl]-3-chloro-2-methoxypyridine

→

3-chloro-2-methoxy-6-[(1E)-3-[4-(methylsulfonyl)phenyl]-1-(tetrahydro-2H-pyran-4-yl)prop-1-en-2-yl]pyridine

Ausbeute 59.0%

Lösungsmittel

water

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas returned to room temperature
2. 2
   workup.STIRRINGthe mixture was stirred at 90° C. for two hours
3. 3
   Extraktionfollowed by extraction with ethyl acetate
4. 4
   WaschenThe organic layer was washed with brine
5. 5
   Trocknendried over anhydrous magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   SonstigeThe solvent was then evaporated under reduced pressure
8. 8
   SonstigeThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→0:1)

Vorschrift

1-(Bromomethyl)-4-(methylsulfonyl)benzene (110 mg), trimethylsilyl chloride (12.5 μL) and 1,2-dibromoethane (8.6 μL) were added to a solution of zinc powder (78 mg) in tetrahydrofuran (4 mL) in the presence of an argon gas, and the mixture was stirred at 80° C. for two hours. The reaction solution was returned to room temperature. A solution of tris(dibenzylideneacetone)dipalladium (45 mg), tri(2-furyl)phosphine (69 mg) and 6-[(Z)-1-bromo-2-(tetrahydro-2H-pyran-4-yl)ethenyl]-3-chloro-2-methoxypyridine (380 mg) in tetrahydrofuran (2 mL) was added and the mixture was stirred at 90° C. for two hours. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→0:1) to give 3-chloro-2-methoxy-6-[(1E)-3-[4-(methylsulfonyl)phenyl]-1-(tetrahydro-2H-pyran-4-yl)prop-1-en-2-yl]pyridine as a yellow oil (110 mg).

Quelle