Pyridinium, 1-amino-, iodide (1:1) → HCID 21956522, Verbindung

HRID 2213101Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2213101
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:15]=[CH:16]/[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:6]=[CH:7][C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1.[I-].[NH2:23][N+:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:15]2[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][N:24]3[N:23]=2)[CH:6]=[CH:7][C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1

Komponenten

5

Edukt 2

HCID 2733704Pyridinium, 1-amino-, iodide (1:1)HCID 21956511HCID 21956511, Verbindung

Produkt 1

HCID 21956522HCID 21956522, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of ethyl(2E)-3-(3-methoxy-4-pyridin-2-ylphenyl)prop-2-enoate (55 mg, 0.2 mmol) and 1-aminopyridinium iodide (86 mg, 0.4 mmol) in DMF (1 mL) was stirred at rt for 2 days open to the atmosphere. The deep purple reaction mixture was diluted with CH2Cl2 (25 mL) and washed with a saturated solution of sodium thiosulfate (25 mL) and brine (25 mL), then dried (MgSO4) and concentrated. The residue was purified by flash column chromatography on silica gel eluting with EtOAc:hexanes (1:9 to 3:2) to afford the desired ethyl 2-(3-methoxy-4-pyridin-2-ylphenyl)pyrazolo[1,5-a]pyridin-3-carboxylate as a white solid.

Aufarbeitung

  1. washwashed with a saturated solution of sodium thiosulfate (25 mL) and brine (25 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customThe residue was purified by flash column chromatography on silica gel eluting with EtOAc:hexanes (1:9 to 3:2)

Quellen und Nachweise

ORD-Eintrag
ord-5649251577844a0d8001551b1ae6c183
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07105533B2

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