Sodium hydride → 2-Cyclopropyl-5,7-dimethyl-3-(6-bromopyridin-3-ylmethyl)imidazo[4,5-b]pyridine

HRID 233740

Reaktionsgleichung

Reaktionsgleichung von HRID 233740
[H-].[Na+].[CH:3]1([C:6]2[NH:7][C:8]3[C:9]([N:16]=2)=[N:10][C:11]([CH3:15])=[CH:12][C:13]=3[CH3:14])[CH2:5][CH2:4]1.[Br:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24]Br)=[CH:20][N:19]=1>CS(C)=O.O>[CH:3]1([C:6]2[N:16]([CH2:24][C:21]3[CH:20]=[N:19][C:18]([Br:17])=[CH:23][CH:22]=3)[C:9]3=[N:10][C:11]([CH3:15])=[CH:12][C:13]([CH3:14])=[C:8]3[N:7]=2)[CH2:5][CH2:4]1

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 64246602-Bromo-5-bromomethylpyridineHCID 103134402-Cyclopropyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridine

Produkt 1

HCID 152250222-Cyclopropyl-5,7-dimethyl-3-(6-bromopyridin-3-ylmethyl)imidazo[4,5-b]pyridineAusbeute 69,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

255 mg (6.4 mmol) of sodium hydride and 994 mg (5.3 mmol) of 2-cyclopropyl-5,7-dimethylimidazo[4,5-b]pyridine are stirred at 0° C. for 2 h in 15 ml of dimethyl sulphoxide. After adding 2 g (7.97 mmol) of 2-bromo-5-bromomethylpyridine, the mixture is stirred at room temperature overnight. The reaction mixture is diluted with water and washed twice with ethyl acetate; the combined organic phases are washed with water and sodium chloride solution, dried over sodium sulphate and then chromatographed on 150 g of silica gel using ethyl acetate/petroleum ether mixtures 1:2→1:0 to yield 1.32 g of the title compound.

Aufarbeitung

  1. washwashed twice with ethyl acetate
  2. washthe combined organic phases are washed with water and sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. customchromatographed on 150 g of silica gel

Quellen und Nachweise

ORD-Eintrag
ord-8a4e113514aa465c8b69e6ddfbb6fcf7
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05594010

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