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Methyl iodide → 2-(4-((6-Fluoro-2-quinoxalinyl)oxy)phenoxy)-N-methyl-N-(4-(trifluoromethoxy)phenyl)propanamide

HRID 1655546
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Reaktionsgleichung

Reaktionsgleichung von HRID 1655546
[H-].[Na+].[CH3:3]CCCCC.[F:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[C:15]([O:20][C:21]1[CH:43]=[CH:42][C:24]([O:25][CH:26]([CH3:41])[C:27]([NH:29][C:30]3[CH:35]=[CH:34][C:33]([O:36][C:37]([F:40])([F:39])[F:38])=[CH:32][CH:31]=3)=[O:28])=[CH:23][CH:22]=1)[CH:14]=[N:13]2.CI>CN(C=O)C>[F:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[C:15]([O:20][C:21]1[CH:43]=[CH:42][C:24]([O:25][CH:26]([CH3:41])[C:27]([N:29]([CH3:3])[C:30]3[CH:35]=[CH:34][C:33]([O:36][C:37]([F:40])([F:39])[F:38])=[CH:32][CH:31]=3)=[O:28])=[CH:23][CH:22]=1)[CH:14]=[N:13]2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6328Methyl iodideHCID 8058HexaneHCID 24758Sodium hydrideHCID 197926992-(4-((6-Fluoro-2-quinoxalinyl)oxy)phenoxy)-N-(4-(trifluoromethoxy)phenyl)propanamide

Produkt 1

HCID 197926882-(4-((6-Fluoro-2-quinoxalinyl)oxy)phenoxy)-N-methyl-N-(4-(trifluoromethoxy)phenyl)propanamideAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A mixture of 0.23 g (5.7 mmol) of a 60 percent NaH/oil dispersion and 10 ml of hexane was stirred under N2 for 10 minutes. The hexane was decanted off, replaced with 20 ml of DMF and a solution of 2.0 g (4.1 mmol) of 2-(4-((6-fluoro-2-quinoxalinyl)oxy)phenoxy)-N-(4-(trifluoromethoxy)phenyl)propanamide in 20 ml of DMF was added dropwise over a period of 30 minutes. The mixture was stirred at ambient temperature for 1.5 hours when a solution of 1.45 g (10 mmol) of methyl iodide in 10 ml of DMF was slowly added. The mixture was stirred at ambient temperature for 2 days and then quenched by cautious addition of a few drops of acetic acid and then water. The mixture was poured into water, extracted with three portions of ether and the combined organic layers dried over MgSO4 and evaporated to dryness. The residue was taken up in hot methylcyclohexane, treated with charcoal and filtered and then allowed to cool to give 1.03 g (50 percent) of the above-named product as colorless crystals, m.p. 137°-139° C. (Compound 41)

Aufarbeitung

  1. customThe hexane was decanted off
  2. additionwas slowly added
  3. stirringThe mixture was stirred at ambient temperature for 2 days
  4. customquenched by cautious addition of a few drops of acetic acid
  5. additionThe mixture was poured into water
  6. extractionextracted with three portions of ether
  7. dry with materialthe combined organic layers dried over MgSO4
  8. customevaporated to dryness
  9. additiontreated with charcoal
  10. filtrationfiltered
  11. temperatureto cool

Quellen und Nachweise

ORD-Eintrag
ord-6b5a2750aadb427d9df82f205917f3d5
Quelldatensatz
uspto-grants-1993_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05250690

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