Potassium Carbonate → HCID 23511454, compound

HRID 353770Notes

Reaction equation

HRID 353770 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 (1L) 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-069a291995ea4b638a392d17f16cad98
Source dataset
uspto-grants-2004_06
Patent number
US06756359B2

Reaction notes

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