Tetrahydrofuran → HCID 68996099, Verbindung

HRID 1727763Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1727763
[Br:1][C:2]1[C:3]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:15])=[CH:9][CH:8]=2)=[N:4][NH:5][CH:6]=1.[CH3:23][C:24](C)([O-:26])[CH3:25].[K+].O1CC[CH2:31][CH2:30]1.O1CCCC1Br>CN(C)C=O>[Br:1][C:2]1[C:3]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([NH:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[O:15])=[CH:9][CH:8]=2)=[N:4][N:5]([CH2:23][CH:24]2[CH2:25][CH2:31][CH2:30][O:26]2)[CH:6]=1

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 130702942-BromotetrahydrofuranHCID 23665647Potassium tert-butoxideHCID 178521959HCID 178521959, Verbindung

Produkt 1

HCID 68996099HCID 68996099, VerbindungAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of N-[4-(4-bromo-1H-pyrazol-3-yl)phenyl]-N′-phenylurea (0.28 mmol) in anhydrous N,N-dimethylformamide (6 mL) cooled to 0° C. was added 11.0M potassium tert-butoxide in tetrahydrofuran (1.12 mmol) dropwise. The reaction mixture was stirred for a further 15 minutes in the cold before dropwise addition of tetrahydrofuryl bromide (0.28 mmol). The reaction mixture was stirred at room temperature for 18 h, followed by quenching with saturated aqueous ammonium chloride (1 mL). The reaction mixture was diluted with water (3 mL) and extracted with ethyl acetate (3×5 mL). The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. Gilson reverse phase HPLC afforded the title compound (53%). ESMS [M+H]+: 441.4

Aufarbeitung

  1. stirringThe reaction mixture was stirred at room temperature for 18 h
  2. customby quenching with saturated aqueous ammonium chloride (1 mL)
  3. additionThe reaction mixture was diluted with water (3 mL)
  4. extractionextracted with ethyl acetate (3×5 mL)
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-841c828dacc447e1954f34464e634050
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07495102B2

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