Methyl iodide → (6-bromo-3-methyl-3H-imidazo[4,5-b]pyridin-2-yl)methanol

HRID 1738238Notes

Reaction equation

HRID 1738238 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([CH2:11][OH:12])[NH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].[CH3:15]I>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([CH2:11][OH:12])[N:8]([CH3:15])[C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 24758Sodium hydrideHCID 178519921HCID 178519921, compound

Product 1

HCID 10681601(6-bromo-3-methyl-3H-imidazo[4,5-b]pyridin-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A procedure similar to that described in Preparation 15 was repeated, except that the reaction was conducted using 3.00 g of 6-bromo-2-hydroxymethyl-3H-imidazo-[5,4-b]pyridine (prepared as described in Preparation 58), 0.58 g of sodium hydride (as a 55% by weight dispersion in mineral oil), 0.92 ml of methyl iodide and 60 ml of dimethylformamide. After completion of the reaction with methyl iodide, the reaction mixture was freed from dimethylformamide by distillation under reduced pressure. The residue was diluted with water, after which it was extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous sodium sulfate, after which the solvent was removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 50:1 by volume mixture of ethyl acetate and methanol as the eluent, to give 1.40 g of the title compound, melting at 142-144° C.

Workup

  1. customA procedure similar to that described in Preparation 15
  2. distillationthe reaction mixture was freed from dimethylformamide by distillation under reduced pressure
  3. additionThe residue was diluted with water
  4. extractionafter which it was extracted with ethyl acetate
  5. washThe extract was washed with an aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customafter which the solvent was removed by distillation under reduced pressure
  8. customThe resulting residue was purified by column chromatography through silica gel
  9. additionby volume mixture of ethyl acetate and methanol as the eluent

Sources & evidence

ORD record
ord-ac3318f54b27428395cdf14e3c825b20
Source dataset
uspto-grants-1999_10
Patent number
US05962470

Reaction notes

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