Реакция #955931

Уравнение реакции

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

Выход 97.0%

Растворители

acetonitrile

Условия реакции

Обработка

1. 1
   ДругоеThe solvent was removed under vacuum
2. 2
   workup.DISSOLUTIONthe solid was dissolved in EtOAc
3. 3
   Промывкаwashed successively with aq. NaHCO3 and brine
4. 4
   Сушкаdried over MgSO4
5. 5
   Фильтрацияfiltered
6. 6
   Другоеevaporated
7. 7
   ДругоеThe residue was purified on silica gel

Методика

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).

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