Reaktion #9539

Reaktionsgleichung

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

trimethyl orthobutyrate

→

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

Ausbeute 77.9%

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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 trimethyl orthobutyrate (5.62 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 13.1 g of tert-butyl 4-[(7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]piperidine-1-carboxylate as a white solid, mp 215–216° C.

Quelle