Phthalimide → HCID 23511454, compound

HRID 2055141Notes

Reaction equation

HRID 2055141 reaction equation
[C:1]1(=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=[O:10])[NH:2]1.[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:20]=[CH:21][NH:22][CH:23]=2)=[CH:15][N:14]=1.C(=O)([O-])[O-].[K+].[K+].BrCCCCN1[C:39](=O)[C:38]2=CC=[CH:43][CH:44]=[C:37]2C1=O>CN(C=O)C>[F:12][C:13]1[N:14]=[CH:15][C:16]([C:19]2[N:20]=[CH:21][N:22]([CH2:43][CH2:44][CH2:37][CH2:38][CH2:39][N:2]3[C:3](=[O:10])[C:4]4[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=4)[C:1]3=[O:11])[CH:23]=2)=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 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

2-14-[4-(6-fluoro-pyridin-3-yl)-imidazol-1-ylmethyl]-butyl)-isoindole-1,3-dione. To a solution of 2-fluoro-5-(1H-imidazol-4-yl)-pyridine (1.72 g, 7.3 mmoles) in DMF (15 ml) was added potassium carbonate (5.0 g, 36.4 mmoles) at room temperature under dry conditions. After heating the reaction mixture in a 80° C. oil bath for 1 hour, N-(4-bromobutyl)phthalimide (8.2 g, 29.2 mmoles) was added to the mixture. The solution was left stirring in an 80° C. oil bath for 24 hours. Upon cooling, the reaction was filtered and the solid was washed with ethyl acetate (25 ml). The filterate was diluted with ethyl acetate and washed with NH4Cl (sat.) (50 ml), H2O (50 ml), NaCl (sat.) (75 ml), dried over sodium sulfate, filtered, and concentrated. The crude product was purified by flash 40 chromatography using an initial solvent gradient of 99% DCM, 1% MeOH, and 0.1% TEA (1 L), then a 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 (1.476 g, 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 (25 ml)
  5. additionThe filterate was diluted with ethyl acetate
  6. washwashed with NH4Cl (sat.) (50 ml), H2O (50 ml), NaCl (sat.) (75 ml)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product was purified by flash 40 chromatography

Sources & evidence

ORD record
ord-51cbc0d6b3204bf986d3005caad67585
Source dataset
uspto-grants-2008_02
Patent number
US07332476B2

Reaction notes

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