1-[8-Chloro-2-(3-methoxyphenyl)imidazo[1,2-alpha]pyridin-3-yl]-2-propyn-1-ol → 1-[8-Chloro-2-(3-methoxyphenyl)imidazo[1,2-alpha]pyridin-3-yl]-2-propyn-1-one

HRID 1295877

Reaktionsgleichung

Reaktionsgleichung von HRID 1295877
[Cl:1][C:2]1[C:3]2[N:4]([C:8]([CH:19]([OH:22])[C:20]#[CH:21])=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=3)[N:10]=2)[CH:5]=[CH:6][CH:7]=1>ClCCl.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[C:3]2[N:4]([C:8]([C:19](=[O:22])[C:20]#[CH:21])=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=3)[N:10]=2)[CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 1

HCID 179681531-[8-Chloro-2-(3-methoxyphenyl)imidazo[1,2-alpha]pyridin-3-yl]-2-propyn-1-ol

Produkt 1

HCID 112321611-[8-Chloro-2-(3-methoxyphenyl)imidazo[1,2-alpha]pyridin-3-yl]-2-propyn-1-oneAusbeute 78,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418406HCID 178418406, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1-[8-chloro-2-(3-methoxyphenyl)imidazo[1,2-α]pyridin-3-yl]-2-propyn-1-ol (870 mg, 2.78 mmol) in dichloromethane (150 mL) was added manganese dioxide (9.6 g, 111 mmol) and the resulting suspension was stirred at room temperature for 1.5 hours. The mixture was filtered through Celite. The filtrate was concentrated in vacuo to give 1-[8-chloro-2-(3-methoxyphenyl)imidazo[1,2-α]pyridin-3-yl]-2-propyn-1-one (680 mg, 78%) as a golden foam. 1H NMR (CDCl3): δ 9.66 (d, 1 H), 7.65 (d, 1 H), 7.34 (t, 1 H), 7.28–7.22 (m, 2 H), 7.10 (t, 1 H), 7.02 (m, 1 H), 3.86 (s, 3 H), 2.86 (s, 1 H); MS m/z 311 (M+1).

Aufarbeitung

  1. filtrationThe mixture was filtered through Celite
  2. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-cb086665708042fb88e8bf0819bf558f
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07244740B2

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