Water → 4-[1-(2,4-Difluorophenylcarbamoyl)-1H-indol-5-yloxy]-6,7-dimethoxyquinoline

HRID 387886ノート

反応式

HRID 387886 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][C:11]3[C:20]4[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=4)[N:14]=[CH:13][CH:12]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[F:27][C:28]1[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=1[N:35]=[C:36]=[O:37].O>CN(C)C=O.C(OCC)(=O)C>[F:27][C:28]1[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=1[NH:35][C:36]([N:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][C:11]3[C:20]4[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=4)[N:14]=[CH:13][CH:12]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1)=[O:37]

参加物

7

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 5932582,4-Difluorophenyl isocyanateHCID 221326454-[(1H-Indol-5-yl)oxy]-6,7-dimethoxyquinoline

生成物 1

HCID 589309404-[1-(2,4-Difluorophenylcarbamoyl)-1H-indol-5-yloxy]-6,7-dimethoxyquinoline収率 58.94%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

After dissolving 4-(1H-indol-5-yloxy)-6,7-dimethoxyquinoline (40 mg, 0.1249 mmol, described in WO9717329) in N,N-dimethylformamide (0.7 ml), sodium hydride (10 mg,) was added and the mixture was stirred at room temperature for 15 minutes. 2,4-Difluorophenyl isocyanate (0.018 ml, 0.1561 mmol) was further added, and the mixture was stirred at room temperature for 2 hours. Water was added to the reaction solution, extraction was performed with ethyl acetate, the extract was washed with saturated saline and dried over anhydrous magnesium sulfate, and the filtrate was distilled off under reduced pressure. The obtained crystals were suspended in diethyl ether:ethanol=10:1 and diluted with hexane, and then the crystals were filtered out, washed with diethyl ether:ethanol=10:1 and dried by aspiration to obtain the title compound (35 mg, 0.0736 mmol, 58.94%) as colorless crystals.

後処理

  1. additionwas added
  2. stirringthe mixture was stirred at room temperature for 2 hours
  3. washthe extract was washed with saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe filtrate was distilled off under reduced pressure
  6. additionethanol=10:1 and diluted with hexane
  7. filtrationthe crystals were filtered out
  8. washwashed with diethyl ether
  9. dry with materialethanol=10:1 and dried by aspiration

出典と根拠

ORDレコード
ord-f557ddf97d1a44e1b0c20dfcfb3d9308
出典データセット
uspto-grants-2013_02
特許番号
US08372981B2

反応ノート

読み込み中…