Sodium hydride → 3-{[3-bromo-2-[2-(2-(triphenylmethyl)-2H-tetrazol-5-yl)phenyl]-2H-indazol-5-yl]methyl}-2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridine

HRID 274144Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 274144
[H-].[Na+].[CH2:3]([C:5]1[NH:6][C:7]2[C:8]([N:15]=1)=[N:9][C:10]([CH3:14])=[CH:11][C:12]=2[CH3:13])[CH3:4].[Br:16][C:17]1[N:18]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[C:34]2[N:35]=[N:36][N:37]([C:39]([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[N:38]=2)[N:19]=[C:20]2[C:25]=1[CH:24]=[C:23]([CH2:26]Br)[CH:22]=[CH:21]2>CN(C=O)C>[Br:16][C:17]1[N:18]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[C:34]2[N:35]=[N:36][N:37]([C:39]([C:52]3[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=3)([C:46]3[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=3)[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[N:38]=2)[N:19]=[C:20]2[C:25]=1[CH:24]=[C:23]([CH2:26][N:15]1[C:8]3=[N:9][C:10]([CH3:14])=[CH:11][C:12]([CH3:13])=[C:7]3[N:6]=[C:5]1[CH2:3][CH3:4])[CH:22]=[CH:21]2

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 98153742,6-Dimethyl-8-ethyl-1-deazapurineHCID 200945455-[2-(3-bromo-5-(bromomethyl)-2H-indazol-2-yl)phenyl]-2-(triphenylmethyl)-2H-tetrazol

Produkt 1

HCID 200945263-{[3-bromo-2-[2-(2-(triphenylmethyl)-2H-tetrazol-5-yl)phenyl]-2H-indazol-5-yl]methyl}-2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridineAusbeute 52,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution obtained by adding sodium hydride (15 mg, 0.366 mmol) to 2-ethyl-5,7-dimethyl-1H-imidazo[4,5-b]pyridine (58 mg, 0.333 mmol) in DMF (2 ml) and stirring for 30 minutes was added 5-[2-(3-bromo-5-(bromomethyl)-2H-indazol-2-yl)phenyl]-2-(triphenylmethyl)-2H-tetrazol (0.250 g, 0.370 mmol) as obtained in Reference Example 9. The mixture was stirred at room temperature for 16 hours. After concentration, it was partitioned by ethyl acetate (10 ml) and water (5 ml). The organic layer was dried over magnesium sulfate, and filtered. The filtrate was concentrated, and subjected to flash chromatography on silica gel using a mixed solvent of dichloromethane/methanol (100:1), whereby 0.134 g of 3-{[3 -bromo-2-[2-(2-(triphenylmethyl)-2H-tetrazol-5-yl)phenyl]-2H-indazol-5-yl]methyl}-2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridine was obtained.

Aufarbeitung

  1. customTo a solution obtained
  2. customas obtained in Reference Example 9
  3. stirringThe mixture was stirred at room temperature for 16 hours
  4. concentrationAfter concentration, it
  5. customwas partitioned by ethyl acetate (10 ml) and water (5 ml)
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-7570e873e9f04089a78ba89a0cfb948a
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05387684

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