p-Chlorothiophenol → HCID 86754257、化合物
反応式
[F:1][C:2]1[CH:18]=[CH:17][C:16]2[N:15]([CH3:19])[C:14]3[C:6]([N:7]=[C:8]4[C:13]=3[CH:12]=[CH:11][CH:10]=[CH:9]4)=[C:5]([Cl:20])[C:4]=2[CH:3]=1.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([SH:28])=[CH:24][CH:23]=1>C(OCCO)C>[ClH:20].[F:1][C:2]1[CH:18]=[CH:17][C:16]2[NH+:15]([CH3:19])[C:14]3[C:6]([N:7]=[C:8]4[C:13]=3[CH:12]=[CH:11][CH:10]=[CH:9]4)=[C:5]([S:28][C:25]3[CH:26]=[CH:27][C:22]([Cl:21])=[CH:23][CH:24]=3)[C:4]=2[CH:3]=1参加物
4
実験手順
To a solution of 2-fluoro-5-methyl-11-chloroquindoline from Example 24 (56 mg, 0.209 mmol) in 2-ethoxyethanol (5 mL) was added 4-chlorothiophenol (36 mg, 120 mol %). The reaction mixture was refluxed for 10 min, during which time the reaction mixture became orange and an orange precipitate formed. The reaction mixture was cooled to room temperature, filtered, and the solid was washed with ether and dried, affording 60 mg (73%) of the title compound, mp 254-256° C.; 1H NMR (DMSO-d6) δ 13.18 (s, 1H, NH), 9.00 (dd, 1H, J=4.4, J=5.2), 8.85 (d, 1H, J=8.4), 8.36 (d, 1H, J=8.0), 8.15 (t, 1H, J=7.2), 7.98 (d, 1H, J=8.0), 7.57 (t, 1H, J=7.2), 7.38-7.33 (m, 4H), 5.10 (s, 3H); 13C NMR (DMSO-d6) δ 161.64, 159.15, 146.27, 138.88, 138.15, 134.90, 132.65, 132.35, 132.07, 130.45, 129.66, 128.60, 126.98 122.77, 122.67, 121.67, 121.41, 114.55, 113.64, 109.83, 109.58, 41.29; MS (FAB, m/z) 393 (M+)