Réaction #9537

Équation de réaction

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

Rendement 77.1%

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source