Reaction #2146696

Reaction equation

water

potassium carbonate

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

1-bromo-3-fluoropropane

→

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

Yield 51.9%

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, and then dried over anhydrous sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated
7. 7
   OtherThe resulting crude product was purified by recycle preparative HPLC (HPLC apparatus

Procedure

398 mg (corresponding to 1.89 mmol) of 2-(4′-hydroxyphenyl)imidazo[1,2-a]pyridine was dissolved in 15 mL of N,N-dimethylformamide, and 788 mg (corresponding to 5.7 mmol) of potassium carbonate was added thereto. 260 μL (corresponding to 2.8 mmol) of 1-bromo-3-fluoropropane was added to the resulting mixture, and the mixture was stirred for 20.5 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, and then dried over anhydrous sodium sulfate, filtered and concentrated. The resulting crude product was 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 264 mg (corresponding to 0.98 mmol) of 2-[4′-(3″-fluoropropoxy)phenyl]imidazo[1,2-a]pyridine (hereinafter referred to as Compound 3) (FIG. 4, Step 3).

Source