Réaction #156309

Équation de réaction

6-bromo-3-fluoro-2-methylpyridine

tert-butyl (3R)-3-methylpiperazine-1-carboxylate

sodium tert-butoxide

toluene

→

tert-butyl (3R)-4-(5-fluoro-6-methylpyridin-2-yl)-3-methylpiperazine-1-carboxylate

Rendement 95.8%

Solvants

water

Conditions de réaction

Traitement

1. 1
   TempératureAfter cooling to room temperature
2. 2
   Extractionextracted with ethyl acetate
3. 3
   LavageThe organic layer was washed with saturated brine
4. 4
   Séchagedried over anhydrous magnesium sulfate
5. 5
   AutreThe solvent was evaporated under reduced pressure
6. 6
   Autrethe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate)

Mode opératoire

To a mixture of 500 mg of 6-bromo-3-fluoro-2-methylpyridine, 580 mg of tert-butyl (3R)-3-methylpiperazine-1-carboxylate, 506 mg of sodium tert-butoxide, and 61 mg of 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene and 7.5 mL of toluene was added 48 mg of tris(dibenzylidenacetone)dipalladium (0), followed by stirring at 110° C. for 3 hours. After cooling to room temperature, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to obtain 780 mg of tert-butyl (3R)-4-(5-fluoro-6-methylpyridin-2-yl)-3-methylpiperazine-1-carboxylate.

Source