Dimethylformamide → 6-(2-Methoxyethylcarbonyl)-7-methoxy-4-(1-ethylcarbamoyl-indol-5-yloxy)quinoline

HRID 1433634Notes

Reaction equation

HRID 1433634 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH3:7])[CH:5]=[O:6].COCCN[C:13]([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][C:24]=1[O:25][CH3:26])[N:21]=[CH:20][CH:19]=[C:18]2[O:27][C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)NC=C2)=[O:14].C1(OC(=O)[NH:45][CH2:46][CH3:47])C=CC=CC=1.[C:49]([O:52][CH2:53][CH3:54])(=O)C>O>[CH3:49][O:52][CH2:53][CH2:54][C:13]([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][C:24]=1[O:25][CH3:26])[N:21]=[CH:20][CH:19]=[C:18]2[O:27][C:28]1[CH:36]=[C:35]2[C:7](=[CH:30][CH:29]=1)[N:4]([C:5](=[O:6])[NH:45][CH2:46][CH3:47])[CH:3]=[CH:34]2)=[O:14]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 2802346phenyl N-ethylcarbamateHCID 229365306-(2-Methoxyethylcarbamoyl)-7-methoxy-4-(indol-5-yloxy) quinoline

Product 1

HCID 229370126-(2-Methoxyethylcarbonyl)-7-methoxy-4-(1-ethylcarbamoyl-indol-5-yloxy)quinoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

After adding 60% sodium hydride (10 mg) to dimethylformamide (1 ml), the mixture was stirred at room temperature, 6-(2-methoxyethylcarbamoyl)-7-methoxy-4-(indol-5-yloxy)quinoline (10 mg) was added, and the mixture was stirred for another 15 minutes. Ethylcarbamic acid phenyl ester (43 mg) was then added and the mixture was stirred for 1 hour. Water was added to the reaction solution, extraction was performed with ethyl acetate, and then the organic layer was washed with water and saturated brine in that order and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. Ethyl acetate was used for recrystallization to obtain the title compound (27 mg).

Workup

  1. stirringthe mixture was stirred for another 15 minutes
  2. stirringthe mixture was stirred for 1 hour
  3. washthe organic layer was washed with water and saturated brine in that order
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customEthyl acetate was used for recrystallization

Sources & evidence

ORD record
ord-49b10a53406f402281ee48ada44a21fb
Source dataset
uspto-grants-2009_11
Patent number
US07612092B2

Reaction notes

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