Sodium hydride → HCID 86595838, compound

HRID 2055148Notes

Reaction equation

HRID 2055148 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18]N3C(=O)C4C(=CC=CC=4)C3=O)[NH:12][C:13]=2[CH3:14])=[CH:5][CH:4]=1.[H-].[Na+].COC1C=CC(C2N=CNC=2C)=CN=1.BrCCCC[N:51]1[C:55](=[O:56])[C:54]2=[CH:57][CH:58]=[CH:59][CH:60]=[C:53]2[C:52]1=[O:61]>CN(C=O)C>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][C:57]3[CH:58]=[CH:59][CH:60]=[C:53]4[C:54]=3[C:55](=[O:56])[NH:51][C:52]4=[O:61])[NH:12][C:13]=2[CH3:14])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 93575N-(4-Bromobutyl)phthalimideHCID 11715314HCID 11715314, compoundHCID 21074542HCID 21074542, compound

Product 1

HCID 86595838HCID 86595838, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

2-{4-[4-(6-methoxy(3-pyridyl))-5-methylimidazolyl]butyl}-isoindole-1,3-dione. To a solution of sodium hydride, 60% dispersion (1.8 g, 44.75 mmoles) in DMF (9 ml) at 0° C. was added a solution of 2-methoxy-5-(5-methylimidazol-4-yl)pyridine (3.4 g, 17.9+mmoles) in DMF (18 ml) dropwise. A solution of N-(4-bromobutyl)phthalimide (7.6 g, 26.9 mmoles) in DMF (12 ml) was than added. The reaction was held at 0° C. for 22 hours, at which time it was dumped onto ice (400 g). 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 a solvent gradient of 0-1-3% MeOH in CH2Cl2 with 0.1% TEA to yield 2-{4-[4-(6-methoxy(3-pyridyl))-5-methylimidazolyl]butyl-isoindole-1,3-dione (1.6 g, 24%). MH+(391)

Workup

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

Sources & evidence

ORD record
ord-0a00b2f3e0cc4670874a64663230828d
Source dataset
uspto-grants-2008_02
Patent number
US07332476B2

Reaction notes

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