반응 #44266

반응 방정식

6-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline

tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate

CsF

CH2Cl2

→

6-((6-(1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline

수율 63.0%

용매

Water

DME

반응 조건

후처리

1. 1
   기타was degassed
2. 2
   기타by bubbling in Argon for 10 minutes
3. 3
   기타The mixture was transferred via syringe
4. 4
   기타The vial was capped
5. 5
   기타reaction mixture
6. 6
   여과the resulting suspension was filtered
7. 7
   세척The precipitate was washed with water and air
8. 8
   기타dried
9. 9
   기타The precipitate was purified by column chromatography
10. 10
    세척elution with methanol and dichloromethane

실험 절차

A mixture of DME (3.0 mL) and 1 M aqueous CsF (0.88 mL) was degassed by bubbling in Argon for 10 minutes. The mixture was transferred via syringe to a vial containing 6-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline (100 mg, 0.29 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (95 mg, 0.32 mmol) and Pd(dppf)2Cl2.CH2Cl2 (6.1 mg, 0.01 mmol). The vial was capped and heated to 80° C. for 16 hours. Water (5 mL) was added to the crude reaction mixture and the resulting suspension was filtered. The precipitate was washed with water and air dried. The precipitate was purified by column chromatography using gradient elution with methanol and dichloromethane to afford 6-((6-(1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline (60 mg, 62%).

출처