反应 #156297

反应方程式

N-{4-bromo-2-[(2E)-3-(dimethylamino)prop-2-enoyl]-5-(trifluoromethyl)phenyl}-2,2,2-trifluoroacetamide

tetrahydro-2H-pyran-4-ylhydrazine dihydrochloride

N-methylpyrrolidone

DIPEA

→

N-{4-bromo-2-[1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-5-yl]-5-(trifluoromethyl)phenyl}-2,2,2-trifluoroacetamide

收率 42.1%

溶剂

water

反应条件

后处理

1. 1
   workup.STIRRINGby stirring at 110° C. for 1 hour
2. 2
   萃取followed by extraction with isopropyl acetate
3. 3
   洗涤the organic layer was washed with saturated brine
4. 4
   其他The solvent was evaporated under reduced pressure
5. 5
   其他the residue was purified by silica gel column chromatography (chloroform/methanol)
6. 6
   其他The obtained oil was triturated with diethyl ether/n-hexane

实验过程

To a mixture of 6.0 g of tetrahydro-2H-pyran-4-ylhydrazine dihydrochloride and 175 mL of N-methylpyrrolidone was added 11 mL of DIPEA, followed by stirring at room temperature for 20 minutes. To the reaction mixture was added 8.86 g of N-{4-bromo-2-[(2E)-3-(dimethylamino)prop-2-enoyl]-5-(trifluoromethyl)phenyl}-2,2,2-trifluoroacetamide, followed by stirring at 110° C. for 1 hour. To the reaction mixture was added water, followed by extraction with isopropyl acetate, and the organic layer was washed with saturated brine. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (chloroform/methanol). The obtained oil was triturated with diethyl ether/n-hexane to obtain 4.19 g of N-{4-bromo-2-[1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-5-yl]-5-(trifluoromethyl)phenyl}-2,2,2-trifluoroacetamide.

来源