تفاعل #955931

معادلة التفاعل

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

المردود 97.0%

المذيبات

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   أخرىThe solvent was removed under vacuum
2. 2
   workup.DISSOLUTIONthe solid was dissolved in EtOAc
3. 3
   غسيلwashed successively with aq. NaHCO3 and brine
4. 4
   تجفيفdried over MgSO4
5. 5
   ترشيحfiltered
6. 6
   أخرىevaporated
7. 7
   أخرىThe residue was purified on silica gel

الإجراء التجريبي

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).

المصدر