Ammonia → 6-bromo-2-methoxy-3-(4-methyl-1H-imidazol-1-yl)pyridine

HRID 546758Notes

Reaction equation

HRID 546758 reaction equation
C([O-])(=O)C.[NH4+:5].[Br:6][C:7]1[N:12]=[C:11]([O:13][CH3:14])[C:10]([N:15]([CH2:18][C:19](=O)[CH3:20])[CH:16]=O)=[CH:9][CH:8]=1.C(OCC)(=O)C.N>C(O)(=O)C>[Br:6][C:7]1[N:12]=[C:11]([O:13][CH3:14])[C:10]([N:15]2[CH:18]=[C:19]([CH3:20])[N:5]=[CH:16]2)=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8857Ethyl AcetateHCID 517165Ammonium AcetateHCID 58351061HCID 58351061, compound

Product 1

HCID 576093006-bromo-2-methoxy-3-(4-methyl-1H-imidazol-1-yl)pyridineYield 58%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
130 °C

Procedure

A suspension of ammonium acetate (267 g) and N-(6-bromo-2-methoxypyridin-3-yl)-N-(2-oxopropyl)formamide (199 g) in glacial acetic acid (400 ml) was stirred at 130° C. for one hour and 10 minutes. The reaction solution was returned to room temperature. Ethyl acetate and ice water were added to the reaction solution, and the reaction solution was ice-cooled. Then, concentrated aqueous ammonia (500 ml) was added dropwise and then the organic layer was separated. The resulting organic layer was sequentially washed with water and brine and dried over anhydrous magnesium sulfate. Then, the organic layer was purified by short silica gel column chromatography (carrier: Wakogel C-200; elution solvent: ethyl acetate). The eluted fraction was concentrated. The resulting residue was triturated with ethyl acetate and tert-butyl methyl ether and dried under reduced pressure to obtain 107.7 g of the title compound.

Workup

  1. customwas returned to room temperature
  2. temperaturecooled
  3. customthe organic layer was separated
  4. washThe resulting organic layer was sequentially washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThen, the organic layer was purified by short silica gel column chromatography (carrier: Wakogel C-200; elution solvent: ethyl acetate)
  7. concentrationThe eluted fraction was concentrated
  8. customThe resulting residue was triturated with ethyl acetate and tert-butyl methyl ether
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-b949c476ceae4e75b4ac705f68a11d3e
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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