Iodo benzene diacetate → 8-(Tert-butyldimethylsilyloxy)-2-(7-methyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline

HRID 876465Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 876465
[Si:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16](/[CH:19]=[N:20]/[NH:21][C:22]1[CH:27]=[C:26]([CH3:28])[CH:25]=[CH:24][N:23]=1)[CH:15]=[CH:14]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>C(Cl)Cl>[Si:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([C:19]1[N:23]3[CH:24]=[CH:25][C:26]([CH3:28])=[CH:27][C:22]3=[N:21][N:20]=1)[CH:15]=[CH:14]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 12217721Iodo benzene diacetateHCID 67230767N-[(E)-[8-[tert-butyl(dimethyl)silyl]oxyquinolin-2-yl]methylideneamino]-4-methylpyridin-2-amine

Produkt 1

HCID 672296368-(Tert-butyldimethylsilyloxy)-2-(7-methyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolineAusbeute 82,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(E)-8-(tert-Butyldimethylsilyloxy)-2-((2-(4-methylpyridin-2-yl)hydrazono)methyl)quinoline (0.720 g, 1.83 mmol) was suspended in DCM (6 mL) at ambient temperature. Iodobenzene diacetate (0.650 g, 2.02 mmol) was added and the solution was allowed to stir at ambient temperature overnight. The mixture was concentrated to an orange oil and purified directly by column chromatography (20% EtOAc/DCM to 50% EtOAc/DCM) to provide the desired product (0.590 g, 82%).

Aufarbeitung

  1. concentrationThe mixture was concentrated to an orange oil
  2. custompurified directly by column chromatography (20% EtOAc/DCM to 50% EtOAc/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-32400bb7b62a4bf7901c8d8e3bae6366
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987251B2

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