Triethylamine → 4-(8-Bromo-2,3-dihydro-2-oxo-1H-imidazo(4,5-c)quinolin-1-yl)-alpha,alpha-dimethylbenzeneacetonitrile

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Reaction Steps

A solution of 5 g (13.1 mmol) of 2-[4-(3-amino-6-bromo-quinolin-4-ylamino)-phenyl]-2-methyl-propionitrile (Example 1g) and 1.59 g (15.7 mmol) of triethylamine in 120 ml CH2Cl2 is added over 40 min to a solution of 2.85 g (14.4 mmol) of trichloromethyl chloroformate (Fluka, Buchs, Switzerland) in 80 ml of CH2Cl2 at 0° C. with an ice-bath. The reaction mixture is stirred for 20 min at this temperature then is quenched with sat. aqueous NaHCO3, stirred for 5 min and extracted with CH2Cl2. The organic layer is dried over Na2SO4, filtered and evaporated in vacuo to give crude title compound as a brownish solid. ES-MS: 407, 409 (M+H)+, Br pattern; analytical HPLC: tret=3.05 min (Grad 1).

Provenance & Evidence