Phthalimidine → HCID 57949351, compound

HRID 2427532Notes

Reaction equation

HRID 2427532 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.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:17]([O:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31]CCl)=[CH:27][CH:26]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(#N)C>[CH2:17]([O:24][C:25]1[CH:26]=[CH:27][C:28]([CH2:31][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:29][CH:30]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 10199PhthalimidineHCID 10796Cesium carbonateHCID 20540370HCID 20540370, compound

Product 1

HCID 57949351HCID 57949351, compoundYield 166%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2,3-dihydro-isoindol-1-one (100 mg, 0.751 mmol) was dissolved in anhydrous acetonitrile and cesium carbonate (730 mg, 0.225 mmol) and 1-benzyloxy-4-chloroethylbenzene (349 mg, 0.150 mmol) were added to the solution and stirred at room temperature for 12 hours. The reaction was partitioned between ethyl acetate and water and the organic was washed with brine, dried over anhydrous sodium sulphate and concentrated. The compound was purified by column chromatography (20% ethyl acetate/hexanes) to yield a yellow solid (82 mg, 33%). 1H NMR (300 MHz, CDCl3): δ 7.91 (d, 1H), 7.37-7.53 (m, 9H), 7.25-7.28 (m, 1H), 6.95 (d, 2H), 5.06 (d, 2H), 4.77 (d, 2H), 4.27 (d, 2H).

Workup

  1. customThe reaction was partitioned between ethyl acetate and water
  2. washthe organic was washed with brine
  3. dry with materialdried over anhydrous sodium sulphate
  4. concentrationconcentrated
  5. customThe compound was purified by column chromatography (20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-bb77eca1a67f45e7b47470b74cf391ad
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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