反应 #2328989

反应方程式

5-(6-Methoxy-1,3-benzoxazol-2-yl)-N-methylpyridin-2-amine

HCl

→

title compound

收率 22.8%

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

收率 22.8%

溶剂

diethylether

CH2Cl2

反应条件

后处理

1. 1
   其他The solvent was removed in vacuo and hydrogen bromide (48% aq., 2 mL)
2. 2
   workup.ADDITIONwas added
3. 3
   萃取extracted twice with ethyl acetate
4. 4
   洗涤The combined organic layers were washed with brine
5. 5
   干燥dried (MgSO4)
6. 6
   过滤filtered
7. 7
   其他evaporated in vacuo
8. 8
   其他The crude product was purified by preparative HPLC

实验过程

5-(6-Methoxy-1,3-benzoxazol-2-yl)-N-methylpyridin-2-amine (50 mg, 0.20 mmol) was dissolved in CH2Cl2 (10 mL) and made acidic with 2M HCl in diethylether. The solvent was removed in vacuo and hydrogen bromide (48% aq., 2 mL) was added. The reaction was run in a microwave reactor at 120° C. for 15 minutes. The mixture was then made basic with sodium bicarbonate and extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated in vacuo. The crude product was purified by preparative HPLC, to give the title compound (11 mg) as a white solid. 1H NMR δ ppm 9.95 (br. s, 1H) 8.72 (d, 1H) 7.99 (dd, 1H) 7.46 (d, 1 H) 7.28 (d, 1 H) 7.03 (d, 1H) 6.79 (dd, 1H) 6.58 (d, 1H) 2.85 (d, 3H); MS m/z (M+H) 242, (M−H) 240.

来源