Ethanol → 5-(4-chlorophenyl)-6-(2,4-dichloro-phenyl)-4-ethoxy-1-phenyl-1H-pyrazolo[3,4-b]pyridine

HRID 1693496

反応式

HRID 1693496 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](N)=[C:10]3[CH:24]=[N:23][N:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:11]3=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])=[CH:4][CH:3]=1.N(O[C:35]([CH3:38])([CH3:37])[CH3:36])=O.[CH3:39][CH2:40][OH:41]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]3[CH:24]=[N:23][N:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:11]3=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])=[CH:6][CH:7]=1.[Cl:1][C:2]1[CH:7]=[CH:37][C:35]([C:38]2[C:9]([O:41][CH2:40][CH3:39])=[C:10]3[CH:24]=[N:23][N:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:11]3=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])=[CH:36][CH:3]=1

参加物

5

反応物 3

HCID 702EthanolHCID 10906Tert-Butyl nitriteHCID 116196625-(4-chloro-phenyl)-6-(2,4-dichlorophenyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridin-4-ylamine

生成物 2

HCID 116129435-(4-chlorophenyl)-6-(2,4-dichloro-phenyl)-4-ethoxy-1-phenyl-1H-pyrazolo[3,4-b]pyridineHCID 116838305-(4-Chloro-phenyl)-6-(2,4-dichloro-phenyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridine

反応条件

温度
80 °C

実験手順

A solution of 5-(4-chloro-phenyl)-6-(2,4-dichloro-phenyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridin-4-ylamine (10 mg, 0.022 mol) in EtOH (1 mL) is treated with tert-butyl nitrite (23 mg, 0.22 mol) and heated to 80° C. for 16 hours. After cooling down to room temperature, the mixture is concentrated and purified by preparative thin layer chromatography to provide 5-(4-Chloro-phenyl)-6-(2,4-dichloro-phenyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridine (Example 4) and 5-(4-chlorophenyl)-6-(2,4-dichloro-phenyl)-4-ethoxy-1-phenyl-1H-pyrazolo[3,4-b]pyridine is also obtained as side product (Example 5). Example 4: 1H NMR (CDCl3) δ(ppm) 8.35 (d, 2H), 8.29 (s, 1H), 8.14 (s, 1H), 7.48(t, 2H), 7.37(d, 1H), 7.28 (t, 1H), 7.23-7.17(m, 4H), 7.11(d, 2H); HPLC-MS calculated for C24H14C13N3 (M+H+): 450.0. Found: 450.2. Example 5: 1H NMR (CDCl3) δ(ppm) 8.36(s, 1H), 8.30 (d, 2H), 7.48 (t, 2H), 7.32 (d, 1H), 7.29 (d, 1H), 7.18 (d, 2H), 7.05-7.14(m, 4H), 4.68 (q, 2H), 1.42 (t, 3H); HPLC-MS calculated for C26H18C13N3O (M+H+): 494.1, Found: 494.2.

後処理

  1. temperatureAfter cooling down to room temperature
  2. concentrationthe mixture is concentrated
  3. custompurified by preparative thin layer chromatography

出典と根拠

ORDレコード
ord-3a6bf8f48cdc457483d798ebe9111fcb
出典データセット
uspto-grants-2012_04
特許番号
US08158634B2

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