Reaction #2146701

Reaction equation

water

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

potassium carbonate

1-bromo-3-fluoropropane

→

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

Yield 86.6%

Solvents

chloroform

Conditions

Workup

1. 1
   Otherto remove moisture
2. 2
   workup.DISSOLUTIONwas dissolved in 10 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 purified by recycle preparative HPLC (HPLC apparatus

Procedure

290 mg (corresponding to 1.0 mmol) of 6-bromo-2-(4′-hydroxyphenyl)imidazo[1,2-a]pyridine that was sufficiently dried to remove moisture was dissolved in 10 mL of N,N-dimethylformamide, and 413 mg (corresponding to 3.0 mmol) of potassium carbonate was added thereto. 138 μL (corresponding to 1.5 mmol) of 1-bromo-3-fluoropropane was added to the resulting solution, and then the solution was stirred at room temperature for 20.5 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 a saturated sodium chloride solution, dried over anhydrous sodium sulfate, and 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 302 mg (corresponding to 0.866 mmol) of 6-bromo-2-[4′-(3″-fluoropropoxy)phenyl]imidazo[1,2-a]pyridine (FIG. 7, Step 3).

Source