Potassium Carbonate → HCID 24756928, compound

HRID 1890183Notes

Reaction equation

HRID 1890183 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[F:24][CH2:25][CH2:26]OS(C1C=CC(C)=CC=1)(=O)=O>O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:26][CH2:25][F:24])=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2560192-Fluoroethyl p-ToluenesulfonateHCID 24864014HCID 24864014, compound

Product 1

HCID 24756928HCID 24756928, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

578 mg (corresponding to 2.0 mmol) of 6-bromo-2-(4′-hydroxyphenyl)imidazo[1,2-a]pyridine that was sufficiently dried to remove moisture was dissolved in 20 mL of N,N-dimethylformamide, and 830 mg (corresponding to 6.0 mmol) of potassium carbonate was added thereto. The mixture was supplemented with 510 μL (corresponding to 3.0 mmol) of 2-fluoroethyl-p-toluenesulfonate, and then the solution was stirred at room temperature for 44.5 hours. After the completion of the reaction, the reaction solution was poured into water and extracted three times with chloroform. The combined chloroform layer was washed with water and a saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated. The resulting crude product was purified by flash silica gel column chromatography (elution solvent: chloroform/methanol=100/1), by recycle preparative HPLC (HPLC apparatus: LC-908 (under trade name; manufactured by Japan Analytical Industry Co., Ltd.); column: two JAIGEL 2H (under trade name; manufactured by Japan Analytical Industry Co., Ltd.) connected together; mobile phase: chloroform), and further by preparative TLC (elution solvent: chloroform/methanol=50:1) to obtain 446 mg (corresponding to 1.33 mmol) of 6-bromo-2-[4′-(2″-fluoroethoxy)phenyl]imidazo[1,2-a]pyridine (FIG. 1-6, Step 3).

Workup

  1. customto remove moisture
  2. dissolutionwas dissolved in 20 mL of N,N-dimethylformamide
  3. customAfter the completion of the reaction
  4. extractionextracted three times with chloroform
  5. washThe combined chloroform layer was washed with water
  6. dry with materiala saturated sodium chloride solution, dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting crude product was purified by flash silica gel column chromatography (elution solvent: chloroform/methanol=100/1), by recycle preparative HPLC (HPLC apparatus
  10. washmobile phase: chloroform), and further by preparative TLC (elution solvent: chloroform/methanol=50:1)

Sources & evidence

ORD record
ord-b3e45303904943e699dfab53bcd2d325
Source dataset
uspto-grants-2013_08
Patent number
US08506930B2

Reaction notes

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