Potassium Carbonate → HCID 74819772, compound

HRID 1948877Notes

Reaction equation

HRID 1948877 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][N:11]3[CH:18]=2)=[CH:4][C:3]=1[I:19].C(=O)([O-])[O-].[K+].[K+].[F:26][CH2:27][CH2:28]OS(C1C=CC(C)=CC=1)(=O)=O.[Cl-].[NH4+]>>[F:26][CH2:27][CH2:28][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][N:11]3[CH:18]=2)=[CH:4][C:3]=1[I:19]

Participants

5

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 2560192-Fluoroethyl p-ToluenesulfonateHCID 68719554HCID 68719554, compound

Product 1

HCID 74819772HCID 74819772, compoundYield 92.4%

Conditions

Temperature
90 °C

Procedure

366 mg (corresponding to 1.00 mmol) of 2-(4′-hydroxy-3′-iodophenyl)-6-methoxyimidazo[1,2-a]pyridine that was sufficiently dried to remove moisture was dissolved in 10.0 mL of N,N-dimethylformamide, and 415 mg (corresponding to 3.00 mmol) of potassium carbonate was added thereto. The mixture was supplemented with 327 mg (corresponding to 1.50 mmol) of 1-fluoro-2-paratoluenesulfonyloxyethane, and then the solution was stirred at 90° C. for 2 hours. After the completion of the reaction, a saturated aqueous ammonium chloride solution was added thereto, and extracted three times with ethyl acetate. The combined ethyl acetate layers were washed with water and a saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=½), to obtain 381 mg (corresponding to 0.924 mmol) of 2-[4′-(2″-fluoroethoxy)-3′-iodophenyl]-6-methoxyimidazo[1,2-a]pyridine (FIG. 5, Step 2).

Workup

  1. customto remove moisture
  2. dissolutionwas dissolved in 10.0 mL of N,N-dimethylformamide
  3. customAfter the completion of the reaction
  4. extractionextracted three times with ethyl acetate
  5. washThe combined ethyl acetate layers were washed with water
  6. dry with materiala saturated sodium chloride solution, dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting crude product was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=½)

Sources & evidence

ORD record
ord-2eae839c0be549bfa04f6a34a81e3bce
Source dataset
uspto-grants-2013_03
Patent number
US08399672B2

Reaction notes

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