Potassium Carbonate → Methyl 2-(1,3-dioxo-5-(pyridin-3-ylmethoxy)isoindolin-2-yl)acetate

HRID 571332Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 571332
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[C:5]2=[O:17].C([O-])([O-])=O.[K+].[K+].Br.Br[CH2:26][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1>CC#N>[O:11]=[C:7]1[C:8]2[C:4](=[CH:3][C:2]([O:1][CH2:26][C:27]3[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=3)=[CH:10][CH:9]=2)[C:5](=[O:17])[N:6]1[CH2:12][C:13]([O:15][CH3:16])=[O:14]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 127070373-(Bromomethyl)pyridine hydrobromideHCID 86681747HCID 86681747, Verbindung

Produkt 1

HCID 86681748Methyl 2-(1,3-dioxo-5-(pyridin-3-ylmethoxy)isoindolin-2-yl)acetateAusbeute 55,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of methyl 2-(5-hydroxy-1,3-dioxoisoindolin-2-yl)acetate (78 mg, 0.332 mmol) in CH3CN (20 mL), K2CO3 (115 mg, 0.829 mmol) and 3-(bromomethyl)-pyridine hydrobromide (126 mg, 0.497 mmol) were added at room temperature. The reaction was heated at 80° C. for 2 hours. The insoluble was filtered off and washed with DCM; the filtrated was evaporated under vacuum; and the crude was partitioned between a saturated solution of Na2CO3 and DCM. The organic phase was washed with brine, dried over sodium sulfate, filtered and evaporated to dryness. The crude was purified by filtration on silica gel cartridge (petroleum ether/EtOAc 1/1 to petroleum ether/EtOAc 2/8) to afford methyl 2-(1,3-dioxo-5-(pyridin-3-ylmethoxy)isoindolin-2-yl)acetate (60 mg, 0.184 mmol, 55.4% yield, MS/ESI+ 327.0 [MH]+).

Aufarbeitung

  1. filtrationThe insoluble was filtered off
  2. washwashed with DCM
  3. customthe filtrated was evaporated under vacuum
  4. customand the crude was partitioned between a saturated solution of Na2CO3 and DCM
  5. washThe organic phase was washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness
  9. filtrationThe crude was purified by filtration on silica gel cartridge (petroleum ether/EtOAc 1/1 to petroleum ether/EtOAc 2/8)

Quellen und Nachweise

ORD-Eintrag
ord-ef1a2b60d6eb444b88de864de57b1d30
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09024027B2

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