HCID 16128050, Verbindung → HCID 67180116, Verbindung

HRID 2362234Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2362234
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][CH2:10][C:11](=O)[CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:4][CH:3]=1.[N:21]1([C:26]2[CH:27]=[CH:28][C:29]([NH2:32])=[N:30][CH:31]=2)[CH:25]=[CH:24][N:23]=[CH:22]1>C(O)C.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Zn+2]>[N:21]1([C:26]2[CH:27]=[CH:28][C:29]([N:32]3[C:8]([C:5]4[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=4)=[CH:9][CH:10]=[C:11]3[CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:30][CH:31]=2)[CH:25]=[CH:24][N:23]=[CH:22]1

Komponenten

5

Edukt 2

HCID 16128050HCID 16128050, VerbindungHCID 58297650Ethyl 7-(4-bromophenyl)-4,7-dioxoheptanoate

Produkt 1

HCID 67180116HCID 67180116, VerbindungAusbeute 7,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 104671Zinc trifluoromethanesulfonateKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of ethyl 7-(4-bromophenyl)-4,7-dioxoheptanoate (5B) (2.56 g, 7.5 mmol) and 5-(1H-imidazol-1-yl)pyridin-2-amine (1.20 g, 7.5 mmol) in 15 mL of ethanol was added Zn(OTf)2 (8.18 g, 22.5 mmol). The resultant mixture was heated at 120° C. for 4 h under microwave irradiation and then concentrated to dryness. The resultant residue was dissolved in EA, washed with water and brine, dried over MgSO4, concentrated and purified by silica gel column chromatography (PE:EA=6:1) to afford ethyl 3-(1-(5-(1H-imidazol-1-yl)pyridin-2-yl)-5-(4-bromophenyl)-1H-pyrrol-2-yl)propanoate as a brown oil (250 mg, 7.1%).

Aufarbeitung

  1. concentrationconcentrated to dryness
  2. dissolutionThe resultant residue was dissolved in EA
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. custompurified by silica gel column chromatography (PE:EA=6:1)

Quellen und Nachweise

ORD-Eintrag
ord-49f28482e28149f1bf457b2ccc3727d5
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08691816B2

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