HCID 59226503, Verbindung → HCID 59226443, Verbindung

HRID 2046774Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2046774
[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[C:10]1[CH2:15][CH2:14][CH2:13][CH:12]([N:16]2[C:24](=[O:25])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]2=[O:26])[CH:11]=1)([O-])=O>C(O)(=O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[CH:10]1[CH2:15][CH2:14][CH2:13][CH:12]([N:16]2[C:17](=[O:26])[C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:24]2=[O:25])[CH2:11]1

Komponenten

4

Edukt 1

HCID 59226503HCID 59226503, Verbindung

Produkt 1

HCID 59226443HCID 59226443, VerbindungAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a solution of 2-(3-(3-nitropyridin-4-yl)cyclohex-2-enyl)isoindoline-1,3-dione (1.0 equiv.) in acetic acid (0.1 M) was added 10% Pd/C (0.2 equiv.) and the reaction was stirred under a H2 balloon. After 3 days, the reaction was filtered through Celite, washed with ethyl acetate and methanol, the filtrate was diluted with ethyl acetate and washed twice with sat. 2M Na2CO3. The organic phase was dried with magnesium sulfate, filtered and concentrated. The crude material was triturated with hexanes and ethyl acetate to afford 2-(3-(3-aminopyridin-4-yl)cyclohexyl)isoindoline-1,3-dione in 73% yield. LC/MS=322.2 (M+H), Rt=0.64 min.

Aufarbeitung

  1. filtrationthe reaction was filtered through Celite
  2. washwashed with ethyl acetate and methanol
  3. additionthe filtrate was diluted with ethyl acetate
  4. washwashed twice with sat. 2M Na2CO3
  5. dry with materialThe organic phase was dried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material was triturated with hexanes and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-00560a1fc1764a7abf8442bc26cef323
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08592455B2

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