Potassium Carbonate → Phthalimide

HRID 2055142Notes

Reaction equation

HRID 2055142 reaction equation
COC1N=CC(C2N=CN(CCCC[N:18]3[C:26](=[O:27])[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[C:19]3=[O:28])C=2)=CC=1.N1C=C(C2C=CC(OC)=NC=2)N=C1.C(=O)([O-])[O-].[K+].[K+].BrCCCCN1C(=O)C2=CC=CC=C2C1=O>CN(C=O)C>[C:19]1(=[O:28])[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:26](=[O:27])[NH:18]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 93575N-(4-Bromobutyl)phthalimideHCID 116032422-[4-[4-(6-Methoxy-3-pyridinyl)-1H-imidazol-1-yl]butyl]-1H-isoindole-1,3(2H)-dioneHCID 178488785HCID 178488785, compound

Product 1

HCID 6809PhthalimideYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-{4-[4-(6-methoxy-pyridin-3-yl)-imidazol-1-yl]-butyl}-isoindole-1,3-dione. To a solution of 5-(1H-imidazol-4-yl)-2-methoxy-pyridine (6.7 g, 38.3 mmoles) in DMF (80 ml) was added potassium carbonate (26.5 g, 192 mmoles) and N-(4-bromobutyl)phthalimide (43.0 g, 153 mmoles) at room temperature under dry conditions. The solution was left stirring at room temperature for 36 hours. The reaction was filtered and the solid was washed with ethyl acetate (25 ml). The filtrate was diluted with ethyl acetate and washed with NH4Cl (sat.) (50 ml), H20 (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 2-14-[4-(6-methoxy-pyridin-3-yl)-imidazol-1-yl]-butyl)-isoindole-1,3-dione (10.09 g, 70%). MH+(377).

Workup

  1. waitThe solution was left
  2. filtrationThe reaction was filtered
  3. washthe solid was washed with ethyl acetate (25 ml)
  4. additionThe filtrate was diluted with ethyl acetate
  5. washwashed with NH4Cl (sat.) (50 ml), H20 (50 ml), NaCl (sat.) (75 ml)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by flash 40 chromatography

Sources & evidence

ORD record
ord-da53cb2c2e0d41859c0f7bf4409f5ed6
Source dataset
uspto-grants-2008_02
Patent number
US07332476B2

Reaction notes

Loading…