HCID 59226459, Verbindung → HCID 59226506, Verbindung

HRID 1523419Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1523419
[CH3:1][C:2]1([CH3:28])[CH2:7][CH:6]([N:8]2[C:16](=[O:17])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:18])[CH:5]=[C:4]([C:19]2[CH:24]=[CH:23][N:22]=[CH:21][C:20]=2[N+:25]([O-])=O)[CH2:3]1>C(O)(=O)C.[Pd]>[NH2:25][C:20]1[CH:21]=[N:22][CH:23]=[CH:24][C:19]=1[C:4]1[CH2:3][C:2]([CH3:28])([CH3:1])[CH2:7][CH:6]([N:8]2[C:9](=[O:18])[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:16]2=[O:17])[CH:5]=1

Komponenten

4

Edukt 1

HCID 59226459HCID 59226459, Verbindung

Produkt 1

HCID 59226506HCID 59226506, VerbindungAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A solution of 2-(5,5-dimethyl-3-(3-nitropyridin-4-yl)cyclohex-2-enyl)isoindoline-1,3-dione (1 eq) in acetic acid (0.1M) was purged with nitrogen for 10 min. Then 10% Pd/C (0.10 eq) was added. The reaction mixture was stirred at room temperature overnight under an atmosphere of hydrogen. Solids were removed by filtration over celite, then rinsed with EtOAc and MeOH. The filtrate was concentrated, diluted with EtOAc and washed 2× with sat. aq. 2M Na2CO3. The organic layer was dried with MgSO4, filtered, and concentrated. The residue was purified by column (5% methanol in 1:1 ethyl acetate and hexanes) to give 2-(3-(3-aminopyridin-4-yl)-5,5-dimethylcyclohex-2-enyl)isoindoline-1,3-dione (89%). LC/MS (m/z): MH+=348.3, Rt=0.79.

Aufarbeitung

  1. customSolids were removed by filtration over celite
  2. washrinsed with EtOAc and MeOH
  3. concentrationThe filtrate was concentrated
  4. additiondiluted with EtOAc
  5. washwashed 2× with sat. aq. 2M Na2CO3
  6. dry with materialThe organic layer was dried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by column (5% methanol in 1:1 ethyl acetate and hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-5a6fc0317023461f81539ae18c7693aa
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09079889B2

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