反应详情
EQUATION
反应方程式
REACTANTS
反应物
PRODUCTS
产物
AUXILIARIES
试剂、催化剂与溶剂
CONDITIONS
反应条件
- 温度
- 0 °C
PROCEDURE
实验过程
The 5-bromo-3-cyclobutyl-1H-indazole intermediate (1.501 g, 5.97 mmol) was dissolved in anhydrous DMF (25 mL), cooled to 0° C. and treated with a 60% dispersion of sodium hydride in mineral oil (330 mg, 8.26 mmol). The cold bath was removed and the reaction mixture was stirred at room temperature for 2 h after which time iodoethane (1.034 g, 6.62 mmol) was added and the reaction mixture was stirred 8 h. The reaction mixture was then cooled and quenched by addition of a saturated aqueous solution of NH4Cl (10 mL) then extracted with EtOAc (20 mL). The organic extract was dried over MgSO4, filtered, and evaporated to an oil, which was purified by silica gel flash chromatography with a 0-10% EtOAc/hexanes gradient to afford titled compound as a light yellow oil (1.14 g, 68%). 1H NMR (DMSO-d6) 7.90 (s, 1H), 7.58 (d, J=8.5, 1H), 7.44 (d, J=8.5, 1H), 4.35 (q, J=7.2, 2H), 3.85 (pent, J=7.6, 1H), 2.35-2.31 (m, 4H), 2.31-2.02 (m, 1H), 1.99 (m, 1H), 1.35 (t, J=7.6, 3H). LC/MS (Method B) 4.27 min, [M+1]+ 279/281.
WORKUP
后处理
- customThe cold bath was removed
- additionwas added
- temperatureThe reaction mixture was then cooled
- customquenched by addition of a saturated aqueous solution of NH4Cl (10 mL)
- extractionthen extracted with EtOAc (20 mL)
- extractionThe organic extract
- dry with materialwas dried over MgSO4
- filtrationfiltered
- customevaporated to an oil, which
- customwas purified by silica gel flash chromatography with a 0-10% EtOAc/hexanes gradient