반응 #955931

반응 방정식

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

수율 97.0%

용매

acetonitrile

반응 조건

후처리

1. 1
   기타The solvent was removed under vacuum
2. 2
   workup.DISSOLUTIONthe solid was dissolved in EtOAc
3. 3
   세척washed successively with aq. NaHCO3 and brine
4. 4
   건조dried over MgSO4
5. 5
   여과filtered
6. 6
   기타evaporated
7. 7
   기타The residue was purified on silica gel

실험 절차

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).

출처