反応 #2328989

反応方程式

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

HCl

→

title compound

収率 22.8%

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

収率 22.8%

溶媒

diethylether

CH2Cl2

反応条件

後処理

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

実験手順

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.

出典