反应 #2328990

反应方程式

5-(5-methoxy-1,3-benzoxazol-2-yl)-N,N-dimethylpyridin-2-amine

BBr3

NaHCO3

→

title compound

收率 23.7%

2-[6-(Dimethylamino)pyridin-3-yl]-1,3-benzoxazol-5-ol

收率 23.7%

溶剂

dichloromethane

dichloromethane

dichloromethane

反应条件

后处理

1. 1
   workup.ADDITIONwas added
2. 2
   其他The layers were separated
3. 3
   萃取the aqueous phase was extracted with dichloromethane (4×)
4. 4
   干燥The combined organic phases were dried (MgSO4)
5. 5
   过滤filtered
6. 6
   其他the solvents removed in vacuo
7. 7
   其他The crude material was purified by preparative HPLC

实验过程

To a solution of 5-(5-methoxy-1,3-benzoxazol-2-yl)-N,N-dimethylpyridin-2-amine (0.368 mmol) in dichloromethane (2.0 mL) was added BBr3 in dichloromethane (1.84 mmol) at 0° C. under an atmosphere of argon and the reaction stirred for 1 h at 0° C. The reaction mixture was neutralized with NaHCO3 (sat. aq.) and dichloromethane was added. The layers were separated and the aqueous phase was extracted with dichloromethane (4×). The combined organic phases were dried (MgSO4), filtered and the solvents removed in vacuo. The crude material was purified by preparative HPLC to give 22.3 mg of the title compound as a white solid. 1H NMR δ ppm 9.44 (s, 1H), 8.83 (d, 1H), 8.13 (dd, 1H), 7.48 (d, 1H), 7.01 (d, 1H), 6.80 (d, 1H), 6.76 (dd, 1H), 3.14 (s, 6H). MS m/z (M+H) 256.

来源