Epibromohydrin → HCID 178419439, compound

HRID 2218370Notes

Reaction equation

HRID 2218370 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)[NH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].[CH2:20]([CH:22]1[O:24][CH2:23]1)Br>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([O:17][CH2:20][CH:22]4[CH2:23][O:24]4)=[CH:15][CH:16]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 18430EpibromohydrinHCID 24758Sodium hydrideHCID 178515890HCID 178515890, compound

Product 1

HCID 178419439HCID 178419439, compoundYield 23.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

4-(6-Bromo-3H-imidazo[4,5-b]pyridin-2-yl)phenol (2 g, 6.89 mmol) was dissolved in DMF (200 ml) and sodium hydride (0.9 g, 20.67 mmol, 55% in oil) was added. The mixture was stirred at 50° C. for 1 h, and epibromohydrin (0.94 ml, 11.37 mmol) was added dropwise followed by stirring for one h at room temperature. Purification by flash chromatography on silica using ethyl acetate/heptane as eluent afforded the title compound (0.55 g, 23%).

Workup

  1. stirringby stirring for one h at room temperature
  2. customPurification by flash chromatography on silica

Sources & evidence

ORD record
ord-071f44e36a8742d5b772b4871eb55165
Source dataset
uspto-grants-2008_08
Patent number
US07410966B2

Reaction notes

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