Potassium Carbonate → Phthalimide

HRID 2055147Notes

Reaction equation

HRID 2055147 reaction equation
ClC1N=CC(C2N=CN(CCCC[N:17]3[C:25](=[O:26])[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:18]3=[O:27])C=2)=CC=1C.ClC1C(C)=CC(C2N=CNC=2)=CN=1.C(=O)([O-])[O-].[K+].[K+].BrCCCCN1C(=O)C2=CC=CC=C2C1=O>CN(C=O)C>[C:18]1(=[O:27])[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:25](=[O:26])[NH:17]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 93575N-(4-Bromobutyl)phthalimideHCID 21074540HCID 21074540, compoundHCID 178422935HCID 178422935, compound

Product 1

HCID 6809PhthalimideYield 27%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-{4-[4-(6-Chloro-5-methyl-pyridin-3-yl)-imidazol-1-yl]-butyl}-isoindole-1,3-dione. To a solution of 2-chloro-5-(1H-imidazol-4-yl)-3-methyl-pyridine (8.2 g, 42.3 mmoles) in DMF (80 ml) was added potassium carbonate (29 g, 212 mmoles) and N-(4-bromobutyl)phthalimide (30 g, 106 mmoles) at room temperature under dry conditions. The solution was left stirring at room temperature overnight. The reaction was filtered and the resulting clear solution was dumped onto ice (1 L). The precipitate was filtered and the solid was dissolved in DCM. The organic solution was dried over sodium sulfate, filtered and concentrated. The crude product was purified by flash chromatography using first a solvent gradient of 99% DCM, 1% MeOH, and 0.1% TEA, then 97% DCM, 3% MeOH, and 0.1% TEA to yield 2-14-[4-(6-chloro-5-methyl-pyridin-3-yl)-imidazol-1-yl]-butyl)-isoindole-1,3-dione (4.0 g, 27%). MH+(395)

Workup

  1. waitThe solution was left
  2. filtrationThe reaction was filtered
  3. filtrationThe precipitate was filtered
  4. dissolutionthe solid was dissolved in DCM
  5. dry with materialThe organic solution was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-1d2f53316bc44ce2b68059081287829c
Source dataset
uspto-grants-2008_02
Patent number
US07332476B2

Reaction notes

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