تفاعل #44266

معادلة التفاعل

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

المردود 63.0%

المذيبات

Water

DME

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
   أخرىreaction mixture
6. 6
   ترشيحthe resulting suspension was filtered
7. 7
   غسيلThe precipitate was washed with water and air
8. 8
   أخرىdried
9. 9
   أخرىThe precipitate was purified by column chromatography
10. 10
    غسيلelution with methanol and dichloromethane

الإجراء التجريبي

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%).

المصدر