Aniline → HCID 22988087, compound

Participants

Reaction Conditions

Reaction Steps

Aniline (0.03 ml) was added to a stirred mixture of 4-(4-bromophenoxy)-7-methoxy-N-(3-morpholinopropyl)quinoline-6-carboxamide (0.132 g), caesium carbonate (0.23 g), palladium acetate (0.01 g), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.055 g) and toluene (5 ml) and the reaction mixture was stirred and heated to stirred and heated to 100° C. for 16 hours. The mixture was evaporated and the resultant residue was partitioned between ethyl acetate and water. The organic phase was washed with a saturated aqueous sodium chloride solution and dried over magnesium sulphate. The residue was purified by column chromatography on silica using increasingly polar mixtures of methylene chloride and methanol as eluent. There was thus obtained the title compound (0.103 g); NMR Spectrum: (CDCl3) 1.86 (m, 2H), 2.49 (m, 6H), 3.6 (q, 2H), 3.7 (m, 4H), 4.1 (s, 3H), 5.77 (s, 1H), 6.5 (d, 1H), 6.96 (t, 1H), 7.04-7.17 (m, 6H), 7.3 (m, 2H), 7.5 (s, 1H), 8.02 (m, 1H), 8.63 (d, 1H), 9.19 (s, 1H); Mass Spectrum: M+H+ 513.

Provenance & Evidence