Hydrochloric Acid → HCID 86620841, compound

Participants

Reaction Steps

To a cooled (ice bath) and stirred suspension of 2-((R)-indan-1-ylamino)-quinoline-5-carbonitrile (example 80, step A) (285 mg, 1.0 mmol) in THF (5 ml) was added drop wise a 1M solution of 4-fluorophenyl-magnesium bromide (6 ml, 6.0 mmol), the reaction mixture was heated under reflux conditions for 92 h and poured into ice-water (20 ml). 2N HCl (5 ml) was added, the mixture was stirred at room temperature for 10 min, 3 N NaOH (5 ml) was added and the mixture was extracted with ethyl acetate (3×80 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 the title compound as light red foam (210 mg, 55%).

Provenance & Evidence