Reaction #44265

Reaction equation

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

Yield 74.5%

Solvents

dichloromethane

CH2Cl2

Conditions

Workup

1. 1
   Otherwas degassed
2. 2
   Otherby bubbling in Argon for 10 minutes
3. 3
   OtherThe mixture was transferred via syringe
4. 4
   OtherThe vial was capped
5. 5
   OtherThe crude reaction mixture
6. 6
   Washthen washed with water
7. 7
   DryingThe dichloromethane was dried over Na2SO4
8. 8
   Filtrationfiltered
9. 9
   Concentrationconcentrated by rotary evaporation
10. 10
    OtherThe residue was purified by column chromatography
11. 11
    Washelution with ethyl acetate and dichloromethane

Procedure

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%).

Source