Reaction #44268

Reaction equation

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

4-methyl-1H-imidazole

CsF

→

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

Yield 56.0%

Solvents

acetonitrile

water

Conditions

Workup

1. 1
   Filtrationthe resulting suspension was filtered
2. 2
   WashThe precipitate was washed with water
3. 3
   Otherpurified by column chromatography
4. 4
   Washelution with methanol and dichloromethane

Procedure

A mixture of 6-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline (50 mg, 0.15 mmol), 4-methyl-1H-imidazole (36 mg, 0.44 mmol) and CsF (25 mg, 0.16 mmol) in acetonitrile (1.45 mL) was heated in a microwave to 160° C. for 20 minutes. The reaction was diluted with water (5 mL) and the resulting suspension was filtered. The precipitate was washed with water and then purified by column chromatography using gradient elution with methanol and dichloromethane to afford 6-((6-(4-methyl-1H-imidazol-1-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline (28 mg, yield 56%)

Source