Potassium Carbonate → HCID 86681751, compound

HRID 571335Notes

Reaction equation

HRID 571335 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]#[N:12])=[CH:8][CH:9]=2)[C:4](=[O:13])[NH:3]1.Br[CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:11]([C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[C:2](=[O:1])[N:3]([CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:4]2=[O:13])#[N:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 121983335-cyanophthalimide

Product 1

HCID 86681751HCID 86681751, compoundYield 58.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

1,3-Dioxoisoindoline-5-carbonitrile (0.522 g, 3.03 mmol) was dissolved in dry DMF (10 ml), then tert-butyl 2-bromoacetate (0.672 ml, 4.55 mmol) and K2CO3 (0.629 g, 4.55 mmol) were added. The resulting suspension was stirred at 90° C. for 3 hours. The solvent was evaporated under vacuum, and the crude was dissolved in ethyl acetate. The precipitate was filtered and washed with ethyl acetate; the filtrate was evaporated under vacuum and the residue was purified by silica gel flash chromatography (petroleum ether:ethyl acetate=9:1 to 70:30) affording tert-butyl 2-(5-cyano-1,3-dioxoisoindolin-2-yl)acetate (0.507 g, 1.771 mmol, 58.4% yield, MS/ESI+ not detectable [MH]+).

Workup

  1. customThe solvent was evaporated under vacuum
  2. dissolutionthe crude was dissolved in ethyl acetate
  3. filtrationThe precipitate was filtered
  4. washwashed with ethyl acetate
  5. customthe filtrate was evaporated under vacuum
  6. customthe residue was purified by silica gel flash chromatography (petroleum ether:ethyl acetate=9:1 to 70:30)

Sources & evidence

ORD record
ord-8b21416ef1194776bf981cd291d4dab4
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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