反应详情
EQUATION
反应方程式
REACTANTS
反应物
PRODUCTS
生成物
AUXILIARIES
试剂、催化剂与溶剂
CONDITIONS
反应条件
- 温度
- 50 °C
PROCEDURE
实验过程
A mixture of 7-[(2-thienylsulfonyl)amino]-5-(trifluoromethoxy)-1H-indole-2-carboxamide (2.14 g), Lawesson's reagent (2.14 g) and tetrahydrofuran (50 mL) was stirred at 50° C. for 1.5 hr, and heated under reflux for 1.5 hr. The reaction mixture was concentrated, and the residue was washed with diisopropyl ether to give pale-yellow crystals. The obtained crystals were subjected to silica gel column chromatography, and eluted with hexane-ethyl acetate (4:1-1:2, volume ratio) to give yellow crystals. A mixture of the obtained crystals, ethyl but-2-ynoate (1.49 g), tributylphosphine (1.07 g), toluene (30 mL) and tetrahydrofuran (10 mL) was stirred at 70° C. for 5 hr. ethyl but-2-ynoate (900 mg) and tributylphosphine (1.07 g) were added to the mixture, and the mixture was further stirred at room temperature for 2.5 days. The reaction mixture was concentrated, and the residue was subjected to silica gel column chromatography, and eluted with hexane-ethyl acetate (4:1-1:3, volume ratio) to give the title compound (780 mg, yield 28%) as a brown oil.
WORKUP
后处理
- temperatureheated
- temperatureunder reflux for 1.5 hr
- concentrationThe reaction mixture was concentrated
- washthe residue was washed with diisopropyl ether
- customto give pale-yellow crystals
- washeluted with hexane-ethyl acetate (4:1-1:2, volume ratio)
- customto give yellow crystals
- stirringwas stirred at 70° C. for 5 hr
- stirringthe mixture was further stirred at room temperature for 2.5 days
- concentrationThe reaction mixture was concentrated
- washeluted with hexane-ethyl acetate (4:1-1:3, volume ratio)