Реакция #9537

Уравнение реакции

tert-butyl 4-[(3-amino-7-bromoquinolin-4-ylamino)methyl]piperidine-1-carboxylate

triethyl orthopropionate

→

tert-butyl 4-[(7-bromo-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]piperidine-1-carboxylate

Выход 77.1%

Условия реакции

Обработка

1. 1
   КонцентрированиеAfter completion, the reaction mixture was concentrated under reduced pressure
2. 2
   Другоеthe residue was purified by flash column chromatography on silica gel (eluting with 95:5 chloroform:CMA)
3. 3
   Другоеfollowed by recrystallization from ethyl acetate

Методика

The method described in Part A of Examples 142–144 was used to treat tert-butyl 4-[(3-amino-7-bromoquinolin-4-ylamino)methyl]piperidine-1-carboxylate (15.0 g, 34.5 mmol) with triethyl orthopropionate (6.68 g, 37.9 mmol). After completion, the reaction mixture was concentrated under reduced pressure, and the residue was purified by flash column chromatography on silica gel (eluting with 95:5 chloroform:CMA) followed by recrystallization from ethyl acetate to provide 12.6 g of tert-butyl 4-[(7-bromo-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]piperidine-1-carboxylate as a white powder, mp 208–209° C.

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