Reaction #44266

Reaction equation

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

Yield 63.0%

Solvents

Water

DME

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
   Otherreaction mixture
6. 6
   Filtrationthe resulting suspension was filtered
7. 7
   WashThe precipitate was washed with water and air
8. 8
   Otherdried
9. 9
   OtherThe precipitate was purified by column chromatography
10. 10
    Washelution with methanol and dichloromethane

Procedure

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%).

Source