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

HRID 387889Notes

Reaction equation

HRID 387889 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 saline 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 saline
  3. dry with materialdrying over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-cf0d25d3b4cc453390d7132a8707bcbf
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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