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

HRID 1010275Notes

Reaction equation

HRID 1010275 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-b5f409d9550540e7b5b535b0561981e2
Source dataset
uspto-grants-2011_07
Patent number
US07973160B2

Reaction notes

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