反应 #156288

反应方程式

water ethyl acetate

N-{4-bromo-2-[(2E)-3-(dimethylamino)prop-2-enoyl]-5-methylphenyl}acetamide

tetrahydro-2H-pyran-4-ylhydrazine hydrochloride

potassium carbonate

→

N-{4-bromo-5-methyl-2-[1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-5-yl]phenyl}acetamide

收率 56.7%

溶剂

ethanol

反应条件

后处理

1. 1
   workup.STIRRINGby stirring at 80° C. for 16 hours
2. 2
   温度cooling to room temperature
3. 3
   其他the aqueous layer was separated
4. 4
   洗涤The organic layer was washed with water and saturated brine
5. 5
   干燥dried over anhydrous magnesium sulfate
6. 6
   其他The solvent was evaporated under reduced pressure
7. 7
   其他the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate)

实验过程

To a solution of 3.37 g of tetrahydro-2H-pyran-4-ylhydrazine hydrochloride in 120 mL of ethanol was added 3.82 g of powdery potassium carbonate, followed by stirring at room temperature for 30 minutes. To a mixture was added 6 g of N-{4-bromo-2-[(2E)-3-(dimethylamino)prop-2-enoyl]-5-methylphenyl}acetamide, followed by stirring at 80° C. for 16 hours and cooling to room temperature. The mixture was poured into a mixture of water/ethyl acetate, and the aqueous layer was separated. The organic layer was washed with water and 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 3.96 g of N-{4-bromo-5-methyl-2-[1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-5-yl]phenyl}acetamide.

来源