Реакция #9543

Уравнение реакции

Trimethyl orthobutyrate

pyridine hydrochloride

1-(3-amino-7-bromoquinolin-4-ylamino)-2-methylpropan-2-ol

→

1-(7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol

Выход 76.7%

Растворители

toluene

—

Hexanes

Условия реакции

Обработка

1. 1
   Температураthe reaction was heated
2. 2
   Температураat reflux for two hours
3. 3
   ДругоеThe solvent was removed under reduced pressure
4. 4
   workup.DISSOLUTIONthe residue was dissolved in dichloromethane
5. 5
   Промывкаwashed with water
6. 6
   ДругоеThe dichloromethane was removed under reduced pressure until a precipitate
7. 7
   Другоеto form
8. 8
   Другоеthe precipitate was isolated by filtration

Методика

Trimethyl orthobutyrate (11.61 mL, 72.6 mmol) and catalytic pyridine hydrochloride were added to a solution of 1-(3-amino-7-bromoquinolin-4-ylamino)-2-methylpropan-2-ol (22.51 g, 72.6 mmol) in anhydrous toluene (120 mL), and the reaction was heated at reflux for two hours. The solvent was removed under reduced pressure, and the residue was dissolved in dichloromethane and washed with water. The dichloromethane was removed under reduced pressure until a precipitate began to form. Hexanes were added, and the precipitate was isolated by filtration to provide 20.17 g of 1-(7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol.

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