Réaction #2146698

Équation de réaction

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

Rendement 44.1%

Solvants

N,N-dimethylformamide

chloroform

Conditions de réaction

Traitement

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

Mode opératoire

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