반응 #2353874

반응 방정식

sodium hydride

Sodium hydride

piperidin-4-ol

2,5-dibromopyridine

→

5-bromo-2-(piperidin-4-yloxy)-pyridine

수율 58.0%

용매

DMSO

반응 조건

후처리

1. 1
   workup.STIRRINGAfter stirring for 24 hours
2. 2
   workup.STIRRINGAfter stirring for another 24 hours the reaction
3. 3
   기타was partitioned between ethyl acetate and water
4. 4
   기타The phases were separated
5. 5
   추출the aqueous phase was extracted with ethyl acetate
6. 6
   건조The combined organic phases were dried over MgSO4
7. 7
   농축concentrated by rotary evaporation
8. 8
   기타The residue was purified by silica gel chromatography
9. 9
   세척elution of dichloromethane, methanol, ammonium hydroxide

실험 절차

Sodium hydride (56 mg, 2.3 mmol) was added to a solution of piperidin-4-ol (214 mg, 2.11 mmol) in DMSO (8 mL). After stirring for 30 minutes, 2,5-dibromopyridine was added. After stirring for 24 hours, sodium hydride (56 mg, 2.3 mmol) was added. After stirring for another 24 hours the reaction was partitioned between ethyl acetate and water. The phases were separated and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over MgSO4 and concentrated by rotary evaporation. The residue was purified by silica gel chromatography using gradient elution of dichloromethane, methanol, ammonium hydroxide to afford 5-bromo-2-(piperidin-4-yloxy)-pyridine (316 mg, 58%).

출처