Sodium hydride → 6-Bromo-3-[[2-(trimethylsilyl)ethoxy]methyl]-3H-imidazo[4,5-b]pyridine

HRID 861017

Reaction equation

HRID 861017 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].[CH3:13][Si:14]([CH2:17][CH2:18][O:19][CH2:20]Cl)([CH3:16])[CH3:15]>CN(C=O)C.[NH4+].[Cl-]>[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[CH:9][N:8]([CH2:20][O:19][CH2:18][CH2:17][Si:14]([CH3:16])([CH3:15])[CH3:13])[C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 9115786-Bromo-4H-imidazo[4,5-b]pyridineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

Product 1

HCID 193582886-Bromo-3-[[2-(trimethylsilyl)ethoxy]methyl]-3H-imidazo[4,5-b]pyridine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of 6-bromo-3H-imidazo[4,5-b]pyridine (1.0 eq.) (see J. Am. Chem. Soc. 1957, 6421.) in DMF (0.2M) was added NaH (1.4 eq.). The mixture was stirred for 30 min then SEM-Cl (2.0 eq.) was added. The final mixture was stirred for 2 h, poured in saturated aqueous NH4Cl and extracted with EtOAc (2×). The combined organic extracts were washed with water (3×), brine, dried over Na2SO4, filtered and concentrated. Flash chromatography (Hex:EtOAc; 7:3) afforded the title compound as a foam.

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic extracts were washed with water (3×), brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1aba1eec898d468b848cfef32b7a44af
Source dataset
uspto-grants-2006_12
Patent number
US07153968B2

Linked notes

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