Phthalimidine → HCID 57949571, compound

HRID 2427503Notes

Reaction equation

HRID 2427503 reaction equation
[C:1]1(=[O:10])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][NH:2]1.[Br:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19]Br)=[CH:15][CH:14]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C>[Br:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][N:2]2[CH2:3][C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[C:1]2=[O:10])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 10199PhthalimidineHCID 10796Cesium carbonateHCID 693351,4-Bis(bromomethyl)benzene

Product 1

HCID 57949571HCID 57949571, compoundYield 49.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2,3-Dihydroisoindol-1-one (350 mg, 2.63 mmol), 1,4-bis-bromomethylbenzene (3.78 g, 14.3 mmol), Cs2CO3 (3.60 g, 11.1 mmol), in acetonitrile (20 mL), was stirred together at room temperature for 5 hours and 80° C. for 20 minutes. The reaction was partitioned between ethyl acetate and water and the organic layer was washed with brine and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure and the product was purified by column chromatography (30% EtOAc/Hexanes) to afford a white solid (410 mg, 49%). 1H NMR (300 MHz, CDCl3): δ 7.92 (d, 1H), 7.49-7.55 (m, 2H), 7.37-7.42 (m, 3H), 7.28-7.31 (m, 2H), 4.82 (s, 2.03), 4.49 (s, 2H), 4.31 (s, 2H).

Workup

  1. customThe reaction was partitioned between ethyl acetate and water
  2. washthe organic layer was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. customThe solvent was removed under reduced pressure
  5. customthe product was purified by column chromatography (30% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-f59781cff1ef4a74bd20dc8df96bbf67
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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