Cesium carbonate → 4-(6-Chloro-7-methoxy-2,3-dimethyl-4-quinolinyl)-6-(4-morpholinyl)-3,4-dihydro-2H-1,4-benzothiazine 1,1-dioxide

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Reaction Steps

Prepared according to procedure T using 6-morpholin-4-yl-3,4-dihydro-2H-1,4-benzothiazine 1,1-dioxide (0.134 g, 0.5 mmol), 4,6-dichloro-7-methoxy-2,3-dimethylquinoline (0.256 g, 1 mmol), cesium carbonate (0.326 g, 1 mmol), Pd2(dba)3 (0.046 g, 0.05 mmol) and (±) BINAP (0.047 g, 0.075 mmol) in 1,4-dioxane (2 mL). After purification by HPLC 4-(6-chloro-7-methoxy-2,3-dimethyl-4-quinolinyl)-6-(4-morpholinyl)-3,4-dihydro-2H-1,4-benzothiazine 1,1-dioxide was obtained. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.10 (1H, s), 7.60 (1H, s), 7.48-7.54 (1H, m), 6.56 (1H, m), 5.51 (1H, dd, J=1.8, 0.9 Hz), 4.12 (2H, br. s.), 3.93 (3H, s), 3.56 (4H, dd, J=5.1, 4.6 Hz), 2.87 (4H, dd, J=5.3, 4.8 Hz), 2.72 (3H, s), 2.55 (2H, m). Mass Spectrum (ESI) m/e=489 (M+1).

Provenance & Evidence