Water → 6-chloro-3-(4-methoxybenzyl)-3H-imidazo[4,5-c]pyridine

HRID 2409049Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2409049
[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[NH:8][CH:9]=[N:10][C:4]=2[CH:3]=1.[H-].[Na+].Cl[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1.O>C1COCC1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[N:8]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[CH:9]=[N:10][C:4]=2[CH:3]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 218138956-Chloro-3H-imidazo(4,5-c)pyridine

Produkt 1

HCID 866898596-chloro-3-(4-methoxybenzyl)-3H-imidazo[4,5-c]pyridineAusbeute 80,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 6-chloro-3H-imidazo[4,5-c]pyridine (3.50 g, 22.79 mmol) in THF (50 mL) at 0° C. was slowly added sodium hydride (60% dispersion in mineral oil, 1.82 g, 45.58 mmol) in several portions. After stirring at RT for 30 min, 1-(chloromethyl)-4-methoxybenzene (4.30 g, 27.48 mmol) was added and the mixture was stirred at RT for 2 h. The reaction mixture was poured into water (100 mL) and extracted with EtOAc (100 mL×2). The combined extracts were washed with water (100 mL) and brine (50 mL), dried (MgSO4), filtered and evaporated under reduced pressure. The residue was purified by SiO2 chromatography eluting with hexane/EtOAc (1:1) to afford 5.0 g (80%) of 6-chloro-3-(4-methoxybenzyl)-3H-imidazo[4,5-c]pyridine as a white solid. MS (ESI): m/z=274.2 [M+1]+.

Aufarbeitung

  1. customat 0° C.
  2. stirringthe mixture was stirred at RT for 2 h
  3. extractionextracted with EtOAc (100 mL×2)
  4. washThe combined extracts were washed with water (100 mL) and brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue was purified by SiO2 chromatography
  9. washeluting with hexane/EtOAc (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-55fef2f5ead1433592f0812abb40949c
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08815877B2

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