Potassium Iodide → 6-bromo-3-iodo-2-methoxypyridine

HRID 70540Notes

Reaction equation

HRID 70540 reaction equation
N([O-])=O.[Na+].[Br:5][C:6]1[N:11]=[C:10]([O:12][CH3:13])[C:9](N)=[CH:8][CH:7]=1.[I-:15].[K+]>O.Cl>[Br:5][C:6]1[N:11]=[C:10]([O:12][CH3:13])[C:9]([I:15])=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 105361376-Bromo-2-methoxypyridin-3-amineHCID 23668193Sodium Nitrite

Product 1

HCID 582361006-bromo-3-iodo-2-methoxypyridineYield 85.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent3×

Procedure

A solution of sodium nitrite (5.44 g) in water (15 mL) was added dropwise to a suspension of 6-bromo-2-methoxypyridin-3-amine (16.0 g) in concentrated hydrochloric acid (130 mL) and water (175 mL) at an internal temperature of 5° C. or less, and the mixture was stirred as such for 20 minutes. This suspension was added dropwise to a solution of potassium iodide (39.2 g) in water (760 mL) at an internal temperature of 5° C. or less. The mixture was brought to room temperature and then stirred at 60° C. for two hours. The reaction solution was brought to room temperature and then extracted with ethyl acetate. The organic layer was washed with a saturated sodium thiosulfate solution and brine, dried over anhydrous magnesium sulfate and filtered, after which the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5→85:15) to give 6-bromo-3-iodo-2-methoxypyridine as a pale orange powder (21.1 g).

Workup

  1. customwas brought to room temperature
  2. stirringstirred at 60° C. for two hours
  3. customwas brought to room temperature
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with a saturated sodium thiosulfate solution and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationafter which the filtrate was concentrated under reduced pressure
  9. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5→85:15)

Sources & evidence

ORD record
ord-61be5e4e549b4dbbb72b6068190a92c2
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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