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
- 0 °C
PROCEDURE
实验过程
(±)-1-(3-Bromo-5-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)ethanol (1.29 g, 3.18 mmol) was dissolved in methylene chloride (10 mL), cooled to 0° C. and treated with 1,8-diazabicyclo(5.4.0)undec-7-ene (96 μL, 0.64 mmol). The reaction was stirred for 10 min and treated with trichloroacetonitrile (3.19 mL, 31.8 mmol) dropwise over 10 min. The ice bath was removed and the reaction stirred at room temperature for 1 h and concentrated. Flash chromatography on silica gel (5% ethyl acetate/hexanes) gave 1.69 g (77%) as an oil. 1H-NMR (CDCl3, 300 MHz) δ 8.27 (s, 1H), 7.59 (d, J=1.8 Hz, 1H), 7.53 (d, J=1.8 Hz, 1H), 6.58 (q, J=6.6 Hz, 1H), 6.19 (qAB, JAB=11.4 Hz, 2H), 3.50-3.56 (m, 2H), 1.74 (m, 3H), 0.80-0.84 (m, 2H), 0.06 (s, 9H).
WORKUP
后处理
- customThe ice bath was removed
- stirringthe reaction stirred at room temperature for 1 h
- concentrationconcentrated
- customFlash chromatography on silica gel (5% ethyl acetate/hexanes) gave 1.69 g (77%) as an oil