5-Hydroxyindole → 6-Methoxycarbonyl-7-methoxy-4-(5-indolyloxy)quinoline

HRID 387973ノート

反応式

HRID 387973 の反応式
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:16][CH3:17])=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[OH:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][CH:23]=[CH:22]2.C(N(C(C)C)CC)(C)C>CN1CCCC1=O>[CH3:15][O:14][C:12]([C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:16][CH3:17])[N:5]=[CH:4][CH:3]=[C:2]2[O:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][CH:23]=[CH:22]2)=[O:13]

参加物

5

反応物 3

HCID 160545-HydroxyindoleHCID 81531DiisopropylethylamineHCID 22646520Methyl 4-chloro-7-methoxyquinoline-6-carboxylate

生成物 1

HCID 229366056-Methoxycarbonyl-7-methoxy-4-(5-indolyloxy)quinoline収率 29.8%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
130 °C

実験手順

After mixing methyl 4-chloro-7-methoxyquinoline-6-carboxylate (WO0050405, P. 34, 8.5 g, 33.77 mmol), 5-hydroxyindole (7 g), diisopropylethylamine (8.9 ml) and N-methylpyrrolidone (8.9 ml), the mixture was heated and stirred at 130° C. for 5 hours and then at 150° C. for 8 hours. After cooling, the solution was adsorbed onto silica gel and purified with a silica gel column (hexane-ethyl acetate system). Ethanol, diethyl ether and hexane were added to the obtained yellow oil, and crystals precipitated upon standing. These were filtered out, washed with diethyl ether and hexane and dried by aspiration to obtain light yellow crystals (3.506 g, 10.06 mmol, 29.80%).

後処理

  1. temperaturethe mixture was heated
  2. waitat 150° C. for 8 hours
  3. temperatureAfter cooling
  4. custompurified with a silica gel column (hexane-ethyl acetate system)
  5. additionEthanol, diethyl ether and hexane were added to the obtained yellow oil, and crystals
  6. customprecipitated
  7. filtrationThese were filtered out
  8. washwashed with diethyl ether and hexane
  9. customdried by aspiration

出典と根拠

ORDレコード
ord-96b2c3dacce94d768343c16293e79acc
出典データセット
uspto-grants-2013_02
特許番号
US08372981B2

反応ノート

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