반응 #44265

반응 방정식

DME

Na2CO3

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

2-fluorophenylboronic acid

→

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

수율 74.5%

용매

dichloromethane

CH2Cl2

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
   기타The crude reaction mixture
6. 6
   세척then washed with water
7. 7
   건조The dichloromethane was dried over Na2SO4
8. 8
   여과filtered
9. 9
   농축concentrated by rotary evaporation
10. 10
    기타The residue was purified by column chromatography
11. 11
    세척elution with ethyl acetate and dichloromethane

실험 절차

A mixture of DME (3.0 mL) and 1 M aqueous Na2CO3 (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), 2-fluorophenylboronic acid (45 mg, 0.32 mmol) and Pd(dppf)2Cl2.CH2Cl2 (6.2 mg, 0.01 mmol). The vial was capped and heated to 80° C. for 3.5 hours. The crude reaction mixture was diluted with dichloromethane then washed with water. The dichloromethane was dried over Na2SO4, filtered and concentrated by rotary evaporation. The residue was purified by column chromatography using gradient elution with ethyl acetate and dichloromethane to afford 6-((6-(2-fluorophenyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline (77 mg, 74%).

출처