Reaction #2146698

Reaction equation

water

potassium carbonate

2-(4′-hydroxyphenyl)-6-iodoimidazo[1,2-a]pyridine

1-bromo-3-fluoropropane

→

2-[4′-(3″-fluoropropoxy)phenyl]-6-iodoimidazo[1,2-a]pyridine

Yield 44.1%

Solvents

N,N-dimethylformamide

chloroform

Conditions

Workup

1. 1
   OtherAfter the completion of the reaction
2. 2
   Extractionextracted three times with chloroform
3. 3
   WashThe combined chloroform layer was washed with water
4. 4
   Dryinga saturated sodium chloride solution, dried over anhydrous sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated
7. 7
   OtherThe resulting crude product was purified by flash silica gel column chromatography (elution solvent: chloroform)
8. 8
   Otherfurther purified by recycle preparative HPLC (HPLC apparatus

Procedure

673 mg (corresponding to 2.0 mmol) of 2-(4′-hydroxyphenyl)-6-iodoimidazo[1,2-a]pyridine was dissolved in 25 mL of N,N-dimethylformamide, and 831 mg (corresponding to 6.0 mmol) of potassium carbonate was added thereto. 275 μL (corresponding to 3.0 mmol) of 1-bromo-3-fluoropropane was added to the resulting solution, and the solution was stirred for 24 hours at room temperature. 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), and further purified by recycle preparative HPLC (HPLC apparatus: LC-908 (under trade name; manufactured by Japan Analytical Industry Co., Ltd.); column: two of JAIGEL 2H (under trade name; manufactured by Japan Analytical Industry Co., Ltd.) connected together; mobile phase: chloroform), to obtain 349 mg (corresponding to 0.881 mmol) of 2-[4′-(3″-fluoropropoxy)phenyl]-6-iodoimidazo[1,2-a]pyridine (FIG. 5, Step 3).

Source