Methyl iodide → 2-[4-(8-Bromo-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl]-2-methylpropanenitrile

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Reaction Steps

To a solution of 3.45 g (8.47 mmol) of 2-[4-(8-bromo-2-oxo-2,3-dihydro-imidazo[4,5-c]quinolin-1-yl)-phenyl]-2-methyl-propionitrile (Example 1h), 1.8 g (12.7 mmol) of iodomethane (Fluka, Buchs, Switzerland) and 273 mg (0.847 mmol) of tetrabutylammonium bromide (Fluka, Buchs, Switzerland) in 170 ml of CH2Cl2 is added a solution of 508 mg (12.7 mmol) of NaOH (Fluka, Buchs, Switzerland) in 85 ml of H2O. The reaction mixture is stirred for 2 days and 900 mg (6.35 mmol) of iodomethane and 254 mg (6.35 mmol) of NaOH in 5 ml of H2O are added. The reaction mixture is stirred for 1 day at RT. After this time, the reaction is quenched with H2O and extracted with CH2Cl2 (2×). The organic layer is washed with brine, dried over Na2SO4, filtered and evaporated in vacuo to give the title compound as a beige solid. ES-MS: 421, 423 (M+H)+, Br pattern; analytical HPLC: tret=3.15 min (Grad 1).

Provenance & Evidence