反応 #44266

反応方程式

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

収率 63.0%

溶媒

Water

DME

反応条件

後処理

1. 1
   その他was degassed
2. 2
   その他by bubbling in Argon for 10 minutes
3. 3
   その他The mixture was transferred via syringe
4. 4
   その他The vial was capped
5. 5
   その他reaction mixture
6. 6
   ろ過the resulting suspension was filtered
7. 7
   洗浄The precipitate was washed with water and air
8. 8
   その他dried
9. 9
   その他The precipitate was purified by column chromatography
10. 10
    洗浄elution with methanol and dichloromethane

実験手順

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%).

出典