Sodium hydride → 4-Bromo-1-{2-(trityloxy)ethyl}-1H-imidazole

HRID 2277498Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2277498
[Br:1][C:2]1[NH:6][CH:5]=[N:4][CH:3]=1.[H-].[Na+].Br[CH2:10][CH2:11][O:12][C:13]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C.O>[Br:1][C:2]1[N:6]=[CH:5][N:4]([CH2:10][CH2:11][O:12][C:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:3]=1

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 961251H-Imidazole, 4-bromo-HCID 109595312-Bromoethyl trityl ether

Produkt 1

HCID 693507044-Bromo-1-{2-(trityloxy)ethyl}-1H-imidazoleAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of 5-bromo-1H-imidazole as prepared in part A (2.2 g, 15 mmol) in DMF (22 mL) at 0° C. was added NaH (658 mg, 60% dispersion, 2.42 mmol) in small portions. The resulting solution was allowed to warm to r.t. and then stirred for 1 hr. The solution was cooled to 0° C. and 1,1′,1″-[(2-bromoethoxy)methanetriyl]tribenzene (5.5 g, 15 mmol) in DMF (10 mL) was added drop-wise. The resulting solution was allowed to warm to r.t. where stirring continued until the reaction was judged complete by TLC (16 hr). The suspension was diluted with water and extracted with DCM (2×50 mL). The organics were dried (MgSO4), filtered, and concentrated to a solid that was recrystallized (EtOAc/Hex) to give 4.47 g of the title compound (69%).

Aufarbeitung

  1. temperatureThe solution was cooled to 0° C.
  2. temperatureto warm to r.t. where
  3. stirringstirring
  4. customwas judged complete by TLC (16 hr)
  5. extractionextracted with DCM (2×50 mL)
  6. dry with materialThe organics were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated to a solid
  9. customthat was recrystallized (EtOAc/Hex)

Quellen und Nachweise

ORD-Eintrag
ord-0d07b7590e494ced8a0450ef71f6a459
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09133166B2

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