HCID 178524013, compound → HCID 178505462, compound

Participants

Reaction Steps

2-Fluoroquindoline-11-carboxylic acid from Example 71 (4.50 g, 16.1 mmol) was refluxed at 250° C. in diphenyl ether (40 mL) for 4 hours. The mixture was cooled, diluted with petroleum ether (40 mL), and filtered. The filter cake was washed with petroleum ether (100 mL) and dried. The crude material was added to methanol (250 mL) and filtered, washing with additional methanol (2×75 mL). Concentration of the filtrate afforded 2.47 g (65%) of the title compound as a brown solid, mp >246° C.; 1H NMR (DMSO-d6) δ 11.52 (s, 1H), 8.34 (d, J=8, 1H), 8.28 (s, 1H), 8.24 (dd, J=9.2, J=5.6, 1H), 7.90 (dd, J=10, J=2.8, 1H), 7.50-7.65 (m, 3H), 7.29 (t, J=8, 1H); 13C NMR (DMSO-d6) δ 158.96 (J=244), 145.53, 143.97, 140.42, 132.86, 131.22 (J=10), 129.83, 127.25, 121.31, 120.84, 119.54, 116.23 (J=27), 112.47 (J=5.3), 111.58, 110.01 (J=22); MS (EI, m/z) 236.1 (M+).

Provenance & Evidence