18-Crown-6 → Methyl 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2-dihydroquinoline-7-carboxylate

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Reaction Steps

To the 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-7-iodoquinolin-2(1H)-one (48 mg) in an oven-dried flask was added 18-crown-6 (34 mg), sodium t-butoxide (13 mg), tris(dibenzylideneacetone)dipalladium (0) (8.3 mg) and rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (17 mg) and the flask carefully filled with argon. The N,N-dimethyl-N-(2-piperazin-1-ylethyl)amine (17 mg) and THF (2 mL) were then added and the reaction stirred at rt for 16 h. The reaction mixture was then filtered and concentrated and the residue purified by reverse phase HPLC to yield the title compound. 1H NMR (500 Hz, CDCl3): δ 7.62-7.35 (m, 8H); 6.74 (d, J=2.3 Hz, 1H); 6.49 (d, J=9.8 Hz, 1H); 5.86 (d, J=2.1 Hz, 1H); 3.16 (t, J=4.8 Hz, 4H); 2.57 (t, J=5.1 Hz, 4H); 2.53-2.46 (m, 4H), 2.28 (s, 6H). Mass spectrum: m/z 557 (M+H).

Provenance & Evidence