Tetrahydrofuran → 1-benzenesulfonyl-N-4-cyclohexyl-1H-pyrrolo[2,3-b]pyridine-4,5-diamine

HRID 1257590

Reaktionsgleichung

Reaktionsgleichung von HRID 1257590
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([N+:26]([O-])=O)[C:18]([NH:19][CH:20]4[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]4)=[C:13]3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1COCC1>[Pd].C(O)C>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([NH2:26])[C:18]([NH:19][CH:20]4[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]4)=[C:13]3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

5

Edukt 2

HCID 8028TetrahydrofuranHCID 67343455(1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-yl)-cyclohexyl-amine

Produkt 1

HCID 673223971-benzenesulfonyl-N-4-cyclohexyl-1H-pyrrolo[2,3-b]pyridine-4,5-diamineAusbeute 103,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A suspension of (1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-yl)-cyclohexyl-amine (10 g, 25.0 mmol) and palladium on carbon (2.7 g, 10%, wet, Degussa, E101 NE/W) in a 3:1 mixture of THF and ethanol (200 ml) was stirred under a hydrogen atmosphere (2-3 balloons) at 50° C. for 13 h. The reaction mixture was cooled to 25° C. then was filtered through Celite. The filtrate was concentrated under reduced pressure to afford crude 1-benzenesulfonyl-N-4-cyclohexyl-1H-pyrrolo[2,3-b]pyridine-4,5-diamine (9.61 g, 100%) as a rose foam. LCMS (Method G, ESI): RT=0.83 min, m+H=371.2. This material was used in subsequent reactions without additional purification or characterization.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to 25° C.
  2. filtrationthen was filtered through Celite
  3. concentrationThe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a55e68ae36ec4955a745a55093070871
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461328B2

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