Diisopropylamine → HCID 21082690, compound

Participants

Reaction Conditions

Reaction Steps

N,N-Diisopropylamine (0.043 g) was added to a stirred mixture of 3-cyano-4-(4-iodo-2,3-methylenedioxyanilino)-6,7-dimethoxyquinoline (0.2 g), 4-(2-propynyl)-1,1-dioxotetrahydro-4H-thiazine (0.145 g), bis(triphenylphosphine)palladium(II) dichloride (0.071 g), cuprous iodide (0.024 g) and ethyl acetate (10 ml) that had been cooled to −20° C. The resultant mixture was allowed to warm to ambient temperature and was stirred for 16 hours. The reaction mixture was partitioned between ethyl acetate and a saturated aqueous sodium bicarbonate solution. The organic layer was washed with water and with a saturated brine solution, dried over magnesium sulphate and evaporated. The residue was triturated under a mixture of acetonitrile and water. The resultant solid was isolated and dried. There was thus obtained the title compound as a solid (0.05 g); NMR Spectrum: (DMSOd6) 2.97–3.04 (m, 4H), 3.12–3.18 (m, 4H), 3.72 (s, 2H), 3.83 (s, 3), 3.85 (s, 3H), 6.04 (s, 2H), 6.82 (d, 1H), 6.95 (d, 1H), 7.31 (s, 1H), 7.74 (s, 1H), 8.48 (s, 1H), 9.6 (s, 1H); Mass Spectrum: M+H+ 521.

Provenance & Evidence