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Water → 6-Carbamoyl-4-[1-(2,4-difluorophenylcarbamoyl)1H-indol-5-yloxy]-7-methoxyquinoline

HRID 1010266
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1010266
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[N:10]=[CH:9][CH:8]=[C:7]2[O:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][CH:21]=[CH:20]2)(=[O:3])[NH2:2].[H-].[Na+].[F:28][C:29]1[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:30]=1[NH:36][C:37](=O)[O:38]C1C=CC=CC=1.O>CN(C)C=O.O1CCCC1.C(OCC)(=O)C>[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[N:10]=[CH:9][CH:8]=[C:7]2[O:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[N:22]([C:37](=[O:38])[NH:36][C:30]1[CH:31]=[CH:32][C:33]([F:35])=[CH:34][C:29]=1[F:28])[CH:21]=[CH:20]2)(=[O:3])[NH2:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 13733129phenyl N-(2,4-difluorophenyl)carbamateHCID 229364686-Carbamoyl-4-(1H-indol-5-yloxy)-7-methoxyquinoline

Produkt 1

HCID 229370016-Carbamoyl-4-[1-(2,4-difluorophenylcarbamoyl)1H-indol-5-yloxy]-7-methoxyquinolineAusbeute 57,3 %

Reagenzien, Katalysatoren, Lösungsmittel

3
HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

After dissolving 6-carbamoyl-4-(1H-indol-5-yloxy)-7-methoxyquinoline (100 mg, 0.3 mmol) in N,N-dimethylformamide (0.5 ml), there was added sodium hydride (12 mg, 0.3 mmol) while cooling on ice and the mixture was stirred at room temperature for 15 minutes. After adding phenyl N-(2,4-difluorophenyl)carbamate (79 mg, 0.3150 mmol), the mixture was stirred at room temperature for 2 hours. Water was added to the reaction solution, extraction was performed with ethyl acetate and tetrahydrofuran, the extract was washed with saturated brine and dried over anhydrous magnesium sulfate, and the filtrate was distilled off under reduced pressure. The obtained crystals were suspended in ethanol and diluted with hexane, and then the crystals were filtered out, washed with hexane and dried by aspiration to obtain the title compound (84 mg, 0.1718 mmol, 57.28%) as colorless crystals.

Aufarbeitung

  1. temperaturewhile cooling on ice
  2. stirringthe mixture was stirred at room temperature for 2 hours
  3. washthe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe filtrate was distilled off under reduced pressure
  6. additiondiluted with hexane
  7. filtrationthe crystals were filtered out
  8. washwashed with hexane
  9. customdried by aspiration

Quellen und Nachweise

ORD-Eintrag
ord-e8c45db8945542b887bf2f359ac2c01a
Quelldatensatz
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07973160B2

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