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

HRID 853500노트

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HRID 853500 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

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온도
130 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-dc826724275049559bc0a7097848b1b5
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253286B2

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