Potassium Carbonate → HCID 24864012, compound

HRID 910641Notes

Reaction equation

HRID 910641 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]([OH: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]>CN(C)C=O>[F:28][CH2:27][CH2:26][CH2:25][O:16][C:13]1[CH:14]=[CH:15][C:10]2[N:11]([CH:17]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=3)[N:9]=2)[CH:12]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 67699Propane, 1-bromo-3-fluoro-HCID 67337028HCID 67337028, compound

Product 1

HCID 24864012HCID 24864012, compoundYield 0%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

560 mg (corresponding to 2.48 mmol) of 2-(4′-hydroxyphenyl)-6-hydroxyimidazo[1,2-a]pyridine was dissolved in 21 mL of N,N-dimethylformamide, and 1.37 g (corresponding to 9.90 mmol) of potassium carbonate and 349 mg (corresponding to 2.48 mmol) of 1-bromo-3-fluoropropane were added thereto. The solution was stirred at room temperature for 24 hours. The reaction solution was concentrated under reduced pressure, and then supplemented with 10 mL of chloroform and 10 mL of methanol to obtain slurry. The slurry was filtered and filtrate was concentrated. The resulting crude product was purified by silica gel column chromatography (elution solvent: chloroform/methanol=20/1), to obtain 151 mg (corresponding to 0.527 μmol) of 6-(3′-fluoropropoxy)-2-(4′-hydroxyphenyl)imidazo[1,2-a]pyridine (FIG. 5, Step 7).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customto obtain slurry
  3. filtrationThe slurry was filtered
  4. concentrationfiltrate was concentrated
  5. customThe resulting crude product was purified by silica gel column chromatography (elution solvent: chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-0e6580fbe0354ec384fae8656d8c6a7a
Source dataset
uspto-grants-2011_09
Patent number
US08022207B2

Reaction notes

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