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

HRID 2059516Notes

Reaction equation

HRID 2059516 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>CN(C)C=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

7

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 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

673 mg (corresponding to 2.0 mmol) of 2-(4′-hydroxyphenyl)-6-iodoimidazo[1,2-a]pyridine was dissolved in 25 mL of N,N-dimethylformamide, and 831 mg (corresponding to 6.0 mmol) of potassium carbonate was added thereto. 275 μL (corresponding to 3.0 mmol) of 1-bromo-3-fluoropropane was added to the resulting solution, and the solution was stirred for 24 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, 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 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 349 mg (corresponding to 0.881 mmol) of 2-[4′-(3″-fluoropropoxy)phenyl]-6-iodoimidazo[1,2-a]pyridine (FIG. 5, Step 3).

Workup

  1. customAfter the completion of the reaction
  2. extractionextracted three times with chloroform
  3. washThe combined chloroform layer was washed with water
  4. dry with materiala saturated sodium chloride solution, dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting crude product was purified by flash silica gel column chromatography (elution solvent: chloroform)
  8. customfurther purified by recycle preparative HPLC (HPLC apparatus

Sources & evidence

ORD record
ord-f286747f16134b25b6e7fc31688de88b
Source dataset
uspto-grants-2012_10
Patent number
US08277777B2

Reaction notes

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