반응 #560451

반응 방정식

5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazole-3-thiol

ethyl 1-bromocyclobutanecarboxylate

diisopropylethylamine

→

ethyl 1-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)cyclobutanecarboxylate

수율 55.0%

용매

DMF

반응 조건

후처리

1. 1
   농축the mixture was concentrated
2. 2
   기타partitioned between dichloromethane (15 mL) and HCl (1N aqueous, 15 mL)
3. 3
   추출The aqueous layer was extracted with dichloromethane (2×15 mL)
4. 4
   건조the combined organic extracts dried over sodium sulfate
5. 5
   농축concentrated
6. 6
   기타purified by column chromatography (40% EtOAc/hexanes)

실험 절차

A solution of 5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazole-3-thiol (100 mg, 0.289 mmol), ethyl 1-bromocyclobutanecarboxylate (47 μL, 0.289 mmol) and diisopropylethylamine (151 μL, 0.866 mmol) in DMF (1 mL) was heated at 60° C. for 4 days. After cooling to room temperature, the mixture was concentrated and partitioned between dichloromethane (15 mL) and HCl (1N aqueous, 15 mL). The aqueous layer was extracted with dichloromethane (2×15 mL) and the combined organic extracts dried over sodium sulfate, concentrated and purified by column chromatography (40% EtOAc/hexanes) to provide ethyl 1-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)cyclobutanecarboxylate as a light yellow sticky foam (75 mg, 55% yield).

출처