(4-(cyclohexylamino)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)methanol → 4-(cyclohexylamino)-1-tosyl-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde

HRID 1969861Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1969861
[CH:1]1([NH:7][C:8]2[C:13]([CH2:14][OH:15])=[CH:12][N:11]=[C:10]3[N:16]([S:19]([C:22]4[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=4)(=[O:21])=[O:20])[CH:17]=[CH:18][C:9]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH:1]1([NH:7][C:8]2[C:13]([CH:14]=[O:15])=[CH:12][N:11]=[C:10]3[N:16]([S:19]([C:22]4[CH:23]=[CH:24][C:25]([CH3:26])=[CH:27][CH:28]=4)(=[O:21])=[O:20])[CH:17]=[CH:18][C:9]=23)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Komponenten

4

Edukt 1

HCID 58557792(4-(cyclohexylamino)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)methanol

Produkt 1

HCID 585572344-(cyclohexylamino)-1-tosyl-1H-pyrrolo[2,3-b]pyridine-5-carbaldehydeAusbeute 87,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418406HCID 178418406, VerbindungKatalysatorHCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

A mixture of (4-(cyclohexylamino)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)methanol (1.12 g, 2.80 mmol) and manganese dioxide (5.48 g, 63.1 mmol) in chloroform (70 mL) was stirred at ambient temperature for about 18 h. The reaction mixture was diluted with chloroform (100 mL) and the reaction mixture was filtered through a pad of Celite® while washing with chloroform (50 mL). The filtrate was concd under reduced pressure to give 4-(cyclohexylamino)-1-tosyl-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (0.975 g, 87%) as an off white solid: LC/MS (Table 1, Method c) Rt=1.70 min; MS m/z: 398 (M+H)+.

Aufarbeitung

  1. filtrationthe reaction mixture was filtered through a pad of Celite®
  2. washwhile washing with chloroform (50 mL)

Quellen und Nachweise

ORD-Eintrag
ord-b36280f743634acb8392486322e8a037
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426411B2

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