To a cooled (ice bath) and stirred suspension of 2-((R)-indan-1-ylamino)-quinoline-6-carbonitrile (example 53, step B) (230 mg, 0.81 mmol) in tetrahydrofurane (4 ml) was added drop wise a 1M solution of 4-fluorophenyl-magnesium bromide (2.4 ml, 2.43 mmol), the reaction mixture was heated under reflux conditions for 20 h and poured into ice-water (20 ml). 2N hydrochloride solution (5 ml) was added, the mixture was stirred at room temperature for 10 min, 3 N sodium hydroxide solution (5 ml) was added and the mixture was extracted with ethyl acetate (3×100 ml). The combined organic layers were washed with brine (2×50 ml), dried (MgSO4) and evaporated. The crude product was purified by flash chromatography (ethyl acetate/heptane) on silica gel to yield (4-fluoro-phenyl)-[2-((R)-indan-1-ylamino)-quinolin-6-yl]-methanone as light yellow foam (220 mg, 71%). MS: m/e=383.2 (M+H+).
