4-Fluorobenzylamine → 2-((R)-Indan-1-ylamino)-quinoline-6-carboxylic acid 4-fluoro-benzylamide

Participants

Reaction Steps

To a stirred solution of commercially available 4-fluoro-benzylamine (250 mg, 2.0 mmol) in dioxane (10 ml) was added drop wise at room temperature a 2M solution of trimethylaluminum in toluene (1 ml). The reaction mixture was allowed to stir for 1 h at room temperature, a solution of 2-((R)-indan-1-ylamino)-quinoline-6-carboxylic acid ethyl ester (166 mg, 0.5 mmol) in dioxane (4 ml) was added and the reaction mixture was heated for 2 h at 90° C. The reaction mixture was poured into 0.886M sodium-potassium-tartrate solution (25 ml) and extracted with ethyl acetate (2×40 ml). The combined organic layers were washed with brine (25 ml), dried (MgSO4) and evaporated. The crude product was purified by flash chromatography (ethyl acetate/heptane) on silica gel and crystallization (dichloromethane/MeOH/hexane) to yield the title compound as an off-white solid (164 mg, 80%), MS (ISP) 412.2 [(M+H)+]; m.p. 175° C.

Provenance & Evidence