Sodium hydride → 4-[1-(2-Fluoroethylcarbamoyl)1H-indol-5-yloxy]-6,7-dimethoxyquinoline

HRID 1433543Notes

Reaction equation

HRID 1433543 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.[H-].[Na+].[F:27][CH2:28][CH2:29][NH:30][C:31](=O)[O:32]C1C=CC=CC=1>>[F:27][CH2:28][CH2:29][NH:30][C:31]([N: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)=[O:32]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 221326454-[(1H-Indol-5-yl)oxy]-6,7-dimethoxyquinolineHCID 22936733Phenyl (2-fluoroethyl)carbamate

Product 1

HCID 589309434-[1-(2-Fluoroethylcarbamoyl)1H-indol-5-yloxy]-6,7-dimethoxyquinolineYield 18.8%

Procedure

4-(1H-Indol-5-yloxy)-6,7-dimethoxyquinoline (75 mg, 0.3122 mmol), sodium hydride (13 mg, 0.3278 mmol) and phenyl N-(2-fluoroethyl)carbamate (45 mg, 0.3278 mmol) were used for reaction in the same manner as Example 310, followed by extraction with ethyl acetate/tetrahydrofuran, washing with saturated brine and drying over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was adsorbed onto silica gel and subjected to silica gel column chromatography (hexane/ethyl acetate system) to obtain the title compound (24 mg, 0.0586 mmol, 18.78%) as colorless crystals.

Workup

  1. extractionfollowed by extraction with ethyl acetate/tetrahydrofuran
  2. washwashing with saturated brine
  3. dry with materialdrying over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-414ad9c7cb064413836f963c4fb625e0
Source dataset
uspto-grants-2009_11
Patent number
US07612092B2

Reaction notes

Loading…