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
A 50 mL round bottom flask was charged with 4-(2-methoxyphenoxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine (6.38 mL, 0.638 mmol) and dichloromethane (6 mL). The solution was cooled to 0° C., and tribromoborane (0.181 mL, 1.91 mmol) and 1 mL of 2-methyl-2-butene were added. The reaction mixture was stirred at 0° C. for 1 hour. Water and saturated solution of NaHCO3 were added, and the reaction mixture was extracted with EtOAc. The organic layer was dried over magnesium sulfate, filtered and concentrated. The residue was purified on a prepacked silica gel column, eluting with 20-35% EtOAc in hexanes to give 2-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)phenol (0.130 g, 67.4% yield) as light yellow solid. 1H NMR (DMSO) δ 10.90 (bs, 1H), 9.70 (bs, 1H), 8.10 (d, 1H), 7.11 (m, 2H), 7.01 (dd, 1H), 6.87 (dt, 1H), 6.49 (d, 1H), 6.43 (m, 2H), 2.19 (d, 3H); Mass spectrum (esi) m/z=300 (100) (M+H).
WORKUP
后处理
- extractionthe reaction mixture was extracted with EtOAc
- dry with materialThe organic layer was dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified on a prepacked silica gel column
- washeluting with 20-35% EtOAc in hexanes