Réaction #1960537

Équation de réaction

2-hydroxyethyl-p-toluenesulfonate

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

triphenylphosphine

diisopropylazodicarboxylate

→

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

Rendement 12.2%

Solvants

N,N-dimethylformamide

chloroform

Conditions de réaction

Traitement

1. 1
   workup.DISSOLUTIONto completely dissolve the contents
2. 2
   Concentrationthe reaction solution was concentrated
3. 3
   AutreThe resulting crude product was purified by flash silica gel column chromatography (elution solvent: hexane/ethyl acetate=65/35)
4. 4
   FiltrationInsoluble matter in chloroform was filtered out of fractions
5. 5
   workup.ADDITIONcontaining a target compound
6. 6
   AutreFurther, the resulting crude product was purified by recycle preparative HPLC (HPLC apparatus

Mode opératoire

To 10 mL of a solution of 639 mg (corresponding to 2.95 mmol) of 2-hydroxyethyl-p-toluenesulfonate in tetrahydrofran, 388 mg (corresponding to 1.34 mmol) of 6-bromo-2-(4′-hydroxyphenyl)imidazo[1,2-a]pyridine and 780 mg (corresponding to 2.97 mmol) of triphenylphosphine were added. Further, 6 mL of N,N-dimethylformamide was added thereto to completely dissolve the contents. To the reaction mixture, 0.58 mL (corresponding to 2.95 mmol) of diisopropylazodicarboxylate was added. After the reaction mixture was stirred at room temperature for 17 hours, the reaction solution was concentrated. The resulting crude product was purified by flash silica gel column chromatography (elution solvent: hexane/ethyl acetate=65/35). Insoluble matter in chloroform was filtered out of fractions containing a target compound. Further, 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 JAIGEL 2H (under trade name; manufactured by Japan Analytical Industry Co., Ltd.) connected together; mobile phase: chloroform), to obtain 79.7 mg (corresponding to 164 μmol) of 6-bromo-2-[4′-(2″-p-toluenesulfonyloxyethoxy)phenyl]imidazo[1,2-a]pyridine (FIG. 1-3, Step 4).

Source