反応 #955931

反応方程式

2-(bromomethyl)pyridine hydrobromide

5-(2,4-dimethylphenyl)-1,3,4-oxadiazol-2-amine

K2CO3

→

5-(2,4-Dimethylphenyl)-N-(pyridin-2-ylmethyl)-1,3,4-oxadiazol-2-amine

収率 97.0%

溶媒

acetonitrile

反応条件

後処理

1. 1
   その他The solvent was removed under vacuum
2. 2
   workup.DISSOLUTIONthe solid was dissolved in EtOAc
3. 3
   洗浄washed successively with aq. NaHCO3 and brine
4. 4
   乾燥dried over MgSO4
5. 5
   ろ過filtered
6. 6
   その他evaporated
7. 7
   その他The residue was purified on silica gel

実験手順

To a solution of 5-(2,4-dimethylphenyl)-1,3,4-oxadiazol-2-amine (Example 16a) (94.5 mg, 0.5 mmol) in 5 ml of dry acetonitrile was added K2CO3 (207 mg, 1.5 mmol). To the suspension was added 2-(bromomethyl)pyridine hydrobromide (127 mg, 0.5 mmol) and the mixture was stirred at 90° C. overnight. The solvent was removed under vacuum and the solid was dissolved in EtOAc, washed successively with aq. NaHCO3 and brine, dried over MgSO4 filtered and evaporated. The residue was purified on silica gel to give 5-(2,4-Dimethylphenyl)-N-(pyridin-2-ylmethyl)-1,3,4-oxadiazol-2-amine (136 mg, 97%) as a white solid. 1H NMR (300 MHz, CdCl3): δ 2.34 (s, 3H), 2.5 (s, 3H), 5.1 (s, 2H), 7.07-7.08 (m, 2H), 7.21-7.33 (m, 2H), 7.64-7.68 (m, 2H), 8.59-8.60 (d, 1H); MS (M+H, 281).

出典