تفاعل #44265

معادلة التفاعل

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

المردود 74.5%

المذيبات

dichloromethane

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   أخرىwas degassed
2. 2
   أخرىby bubbling in Argon for 10 minutes
3. 3
   أخرىThe mixture was transferred via syringe
4. 4
   أخرىThe vial was capped
5. 5
   أخرىThe crude reaction mixture
6. 6
   غسيلthen washed with water
7. 7
   تجفيفThe dichloromethane was dried over Na2SO4
8. 8
   ترشيحfiltered
9. 9
   تركيزconcentrated by rotary evaporation
10. 10
    أخرىThe residue was purified by column chromatography
11. 11
    غسيلelution with ethyl acetate and dichloromethane

الإجراء التجريبي

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%).

المصدر