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

HRID 1433632Notes

Reaction equation

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]

Participants

Conditions

Temperature: 130 °C

Procedure

After mixing methyl 4-chloro-7-methoxyquinoline-6-carboxylate (WO0050405, 6.34, 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%).

Workup

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

Sources & evidence

ORD record: ord-19611c0921484a309dcadb8624728c7c
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612092B2

Reaction notes

Loading…