Реакция #156288

Уравнение реакции

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

Выход 56.7%

Растворители

ethanol

Условия реакции

Обработка

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

Методика

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.

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