Water → 2-[4'-(3''-Fluoropropoxy)phenyl]-6-iodoimidazo[1,2-a]pyridine

HRID 1873359Notes

Reaction equation

HRID 1873359 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][C:13]([I:16])=[CH:12][N:11]3[CH:17]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][CH2:26][CH2:27][F:28].O>C(Cl)(Cl)Cl>[F:28][CH2:27][CH2:26][CH2:25][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][C:13]([I:16])=[CH:12][N:11]3[CH:17]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 67699Propane, 1-bromo-3-fluoro-HCID 247570112-(4'-Hydroxyphenyl)-6-iodoimidazo[1,2-a]pyridine

Product 1

HCID 247569272-[4'-(3''-Fluoropropoxy)phenyl]-6-iodoimidazo[1,2-a]pyridineYield 44.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

673 mg (corresponding to 2.0 mmol) of 2-(4′-hydroxyphenyl)-6-iodoimidazo[1,2-a]pyridine that was sufficiently dried to remove moisture was dissolved in 25 mL of N,N-dimethylformamide, and 831 mg (corresponding to 6.0 mmol) of potassium carbonate was added thereto. The mixture was supplemented with 275 μL (corresponding to 3.0 mmol) of 1-bromo-3-fluoropropane, and then stirred at room temperature for 24 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 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 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 349 mg (corresponding to 0.881 mmol) of 2-[4′-(3″-fluoropropoxy)phenyl]-6-iodoimidazo[1,2-a]pyridine (FIG. 1-5, Step 3).

Workup

  1. customto remove moisture
  2. dissolutionwas dissolved in 25 mL of N,N-dimethylformamide
  3. customAfter the completion of the reaction
  4. extractionextracted three times with chloroform
  5. washThe combined chloroform layer was washed with water
  6. dry with materiala saturated sodium chloride solution, dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting crude product was purified by flash silica gel column chromatography (elution solvent: chloroform)

Sources & evidence

ORD record
ord-307acc58749f4e768340f314462f9052
Source dataset
uspto-grants-2012_11
Patent number
US08303935B2

Reaction notes

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