Reaction #1960533

Reaction equation

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

potassium carbonate

3-bromo-1-propanol

→

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

Yield 73.4%

Solvents

water

Conditions

Workup

1. 1
   Otherto remove moisture
2. 2
   workup.DISSOLUTIONwas dissolved in 50 mL of N,N-dimethylformamide
3. 3
   OtherAfter the completion of the reaction
4. 4
   Extractionextracted three times with chloroform
5. 5
   WashThe combined chloroform layer was washed with a saturated sodium chloride solution
6. 6
   Dryingdried over anhydrous sodium sulfate
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated
9. 9
   OtherThe resulting crude product was recrystallized from methanol

Procedure

1.45 g (corresponding to 5.0 mmol) of 6-bromo-2-(4′-hydroxyphenyl)imidazo[1,2-a]pyridine that was sufficiently dried to remove moisture was dissolved in 50 mL of N,N-dimethylformamide, and 2.07 g (corresponding to 15.0 mol) of potassium carbonate was added thereto. The mixture was supplemented with 680 μL (corresponding to 7.5 mmol) of 3-bromo-1-propanol, and then the solution was stirred at room temperature for 17 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 a saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated. The resulting crude product was recrystallized from methanol to obtain 1.28 g (corresponding to 3.67 mmol) of 6-bromo-2-[4′-(3″-hydroxypropoxy)phenyl]imidazo[1,2-a]pyridine (FIG. 1-2, Step 3).

Source