HCID 68981956, Verbindung → HCID 57893503, Verbindung

HRID 1821916

Reaktionsgleichung

Reaktionsgleichung von HRID 1821916
[CH2:1]([N:8]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:9]1[N:10]=[CH:11][CH:12]=[C:13]2[CH:17]=[C:16]([CH2:18][OH:19])[NH:15][C:14]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C=Cl.[O-2].[O-2].[Mn+4]>[CH2:20]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]1[N:10]=[CH:11][CH:12]=[C:13]2[CH:17]=[C:16]([CH:18]=[O:19])[NH:15][C:14]=12)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Komponenten

4

Edukt 1

HCID 68981956HCID 68981956, Verbindung

Produkt 1

HCID 57893503HCID 57893503, VerbindungAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418406HCID 178418406, VerbindungKatalysatorHCID 5378701Methyl, chloro-Lösungsmittel

Versuchsvorschrift

[7-(Dibenzylamino)-1H-pyrrolo[2,3-c]pyridin-2-yl]methanol (3.0 g, 8.74 mmol) was dissolved in methylene chlorine (175 mL). Manganese dioxide (8.0 g, 92 mmol) was added and the reaction mixture was stirred at room temperature for 20 h. The slurry was filtered through diatomaceous earth to remove the catalyst, and the filtrate was concentrated to a dark oil. Purification by Biotage chromatography (10-30% ethyl acetate in hexanes) provided 7-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridine-2-carboxaldehyde (1.78 g, 60%) as a yellow oil: 1H NMR (300 MHz, CDCl3) δ4.89 (4H, s), 7.06-7.12 (2H, m), 7.27-7.38 (10H, m), 7.93 (1H, d, J=5.7 Hz), 8.74 (1H, br s), 9.77 (1H, s).

Aufarbeitung

  1. filtrationThe slurry was filtered through diatomaceous earth
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated to a dark oil
  4. customPurification by Biotage chromatography (10-30% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-c1c4f3fb22ea4648afcab6b4086067e5
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07608627B2

Verknüpfte Notizen

Wird geladen…