Phthalimide → 2-(5-(Pyridin-2-yl)pent-4-ynyl)isoindoline-1,3-dione

HRID 422512Notes

Reaction equation

HRID 422512 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]#[C:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1.[C:13]1(=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:22])[NH:14]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[N:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[C:6]#[C:5][CH2:4][CH2:3][CH2:2][N:14]1[C:15](=[O:22])[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:13]1=[O:23]

Participants

5

Reactant 3

HCID 6809PhthalimideHCID 11430Potassium CarbonateHCID 665979292-(5-Bromopent-1-ynyl)pyridine

Product 1

HCID 665985312-(5-(Pyridin-2-yl)pent-4-ynyl)isoindoline-1,3-dioneYield 20.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
150 °C

Procedure

2-(5-bromopent-1-ynyl)pyridine (118 mg, 0.525 mmol), isoindoline-1,3-dione (74 mg, 0.5 mmol) and potassium carbonate (140 mg, 1 mmol) were dissolved in acetone (1 mL). The resulting mixture was heated with microwave at 150° C. for 15 min. The reaction was quenched with water, then acetone was evaporated under reduced pressure. The aqueous layer was extracted with DCM, and the organic layer was washed one time with saturated brine, dried over MgSO4, filtrated and concentrated. Purification by flash chromatography pack 15 g silice 40-60, Cyclohexane/AcOEt: 50/50 to afford 30 mg of 2-(5-(pyridin-2-yl)pent-4-ynyl)isoindoline-1,3-dione (Yield: 20%) as a beige powder (Mp=127-129° C.).

Workup

  1. customThe reaction was quenched with water
  2. customacetone was evaporated under reduced pressure
  3. extractionThe aqueous layer was extracted with DCM
  4. washthe organic layer was washed one time with saturated brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltrated
  7. concentrationconcentrated
  8. customPurification by flash chromatography

Sources & evidence

ORD record
ord-2a85cdebaf8b4a9b84f542acacc743e5
Source dataset
uspto-grants-2012_01
Patent number
US08101637B2

Reaction notes

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