Potassium Carbonate → HCID 23511454, compound

HRID 2055125Notes

Reaction equation

HRID 2055125 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][NH:11][CH:12]=2)=[CH:4][N:3]=1.[C:13](=O)([O-])[O-].[K+].[K+].Br[CH2:20][CH2:21][CH2:22][CH2:23][N:24]1[C:28](=[O:29])[C:27]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:26]2[C:25]1=[O:34]>CN(C=O)C>[F:1][C:2]1[N:3]=[CH:4][C:5]([C:8]2[N:9]=[CH:10][N:11]([CH2:13][CH2:20][CH2:21][CH2:22][CH2:23][N:24]3[C:28](=[O:29])[C:27]4[C:26](=[CH:33][CH:32]=[CH:31][CH:30]=4)[C:25]3=[O:34])[CH:12]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 93575N-(4-Bromobutyl)phthalimideHCID 178505534HCID 178505534, compound

Product 1

HCID 23511454HCID 23511454, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-fluoro-5-(1H-imidazol-4-yl)-pyridine (1 eq) in DMF was added potassium carbonate (5 eq) at room temperature under dry conditions. After heating the reaction mixture in a 80° C. oil bath for 1 hour, N-(4-bromobutyl)phtalimide (4 eq) was added to the mixture. The solution was left stirring in a 80° C. oil bath for 24 hours. Upon cooling, the reaction was filtered and the solid was washed with ethyl acetate. The filterate was diluted with ethyl acetate and washed with NH4Cl (sat.), H2O, NaCl (sat.), dried over sodium sulfate, filtered, and concentrated. The crude product was purified by flash chromatography using an initial solvent gradient of 97% DCM, 3% MeOH, and 0.1% TEA (1 L) to yield 2-{4-[4-(6-fluoro-pyridin-3-yl)-imidazol-1-ylmethyl]-butyl}-isoindole-1,3-dione (55%). MH+(365)

Workup

  1. waitThe solution was left
  2. temperatureUpon cooling
  3. filtrationthe reaction was filtered
  4. washthe solid was washed with ethyl acetate
  5. additionThe filterate was diluted with ethyl acetate
  6. washwashed with NH4Cl (sat.), H2O, NaCl (sat.)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-24a3d1488b2a4770b500b1c99bead57f
Source dataset
uspto-grants-2008_02
Patent number
US07332476B2

Reaction notes

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