反应 #2328988

反应方程式

sodium bicarbonate

N-(2-Hydroxy-4-methoxyphenyl)-6-(methylamino)nicotinamide

acetic acid

→

N-[5-(6-methoxy-1,3-benzoxazol-2-yl)pyridin-2-yl]-N-methylacetamide

title compound

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

溶剂

water

反应条件

后处理

1. 1
   萃取The aqueous solution was extracted three times with diethyl ether
2. 2
   洗涤the combined organic layers were washed with brine
3. 3
   干燥dried (MgSO4)
4. 4
   其他evaporated
5. 5
   其他The crude product was purified first by flash column chromatography (hexane/ethyl acetate-gradient; 30-50% ethyl acetate)

实验过程

N-(2-Hydroxy-4-methoxyphenyl)-6-(methylamino)nicotinamide (0.23 g, 0.84 mmol) was mixed with acetic acid (4 mL) and the reaction was run in a microwave reactor at 200° C. for 25 minutes. The reaction mixture was added to water and made basic with sodium bicarbonate (sat. aq.). The aqueous solution was extracted three times with diethyl ether and the combined organic layers were washed with brine, dried (MgSO4) and evaporated. The crude product was purified first by flash column chromatography (hexane/ethyl acetate-gradient; 30-50% ethyl acetate), followed by preparative HPLC, resulting in the isolation of N-[5-(6-methoxy-1,3-benzoxazol-2-yl)pyridin-2-yl]-N-methylacetamide (6 mg) as a minor product, together with the title compound (0.13 g) as a solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.90 (d, 1H) 8.23 (dd, 1H) 7.59 (d, 1H) 7.10 (d, 1H) 6.94 (dd, 1H) 6.52 (d, 1H) 5.26 (br. s, 1H) 3.89 (s, 3H) 2.82-3.16 (m, 3 H); MS m/z (M+H) 256.

来源