Phenyl isocyanate → 4-[1-(Phenylcarbamoyl)-1H-indol-5-yloxy]-6,7-dimethoxyquinoline

HRID 387887Notes

Reaction equation

HRID 387887 reaction equation
[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.[C:25]1([N:31]=[C:32]=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(OCC)C>[C:25]1([NH:31][C:32]([N:1]2[C:9]3[C:4](=[CH:5][C:6]([O:10][C:11]4[C:20]5[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=5)[N:14]=[CH:13][CH:12]=4)=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 221326454-[(1H-Indol-5-yl)oxy]-6,7-dimethoxyquinoline

Product 1

HCID 589314524-[1-(Phenylcarbamoyl)-1H-indol-5-yloxy]-6,7-dimethoxyquinolineYield 32.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4-(1H-Indol-5-yloxy)-6,7-dimethoxyquinoline (25 mg, 0.0780 mmol) and phenyl isocyanate (0.013 ml, 0.117 mmol) were used for reaction in the same manner as Example 330, the obtained crystals were suspended in diethyl ether:ethanol=10:1, and then the crystals were filtered out, washed with diethyl ether and dried by aspiration to obtain the title compound (11 mg, 0.0250 mmol, 32.09%) as colorless crystals.

Workup

  1. filtrationethanol=10:1, and then the crystals were filtered out
  2. washwashed with diethyl ether
  3. customdried by aspiration

Sources & evidence

ORD record
ord-2f31a21c7dbb4255b3fb711eff8db70d
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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