Iodo benzene diacetate → 2-([1,2,4]Triazolo[4,3-a]pyridin-3-yl)-6-fluoro-8-(triisopropylsilyloxy)quinoline

HRID 876409Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 876409
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:12][Si:13]([CH:20]([CH3:22])[CH3:21])([CH:17]([CH3:19])[CH3:18])[CH:14]([CH3:16])[CH3:15])[CH:11]=1)[N:8]=[C:7]([CH:23]=[N:24][NH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1)[CH:6]=[CH:5]2.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>ClCCl>[N:25]1[N:24]=[C:23]([C:7]2[CH:6]=[CH:5][C:4]3[C:9](=[C:10]([O:12][Si:13]([CH:20]([CH3:21])[CH3:22])([CH:17]([CH3:18])[CH3:19])[CH:14]([CH3:15])[CH3:16])[CH:11]=[C:2]([F:1])[CH:3]=3)[N:8]=2)[N:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=12

Komponenten

4

Edukt 2

HCID 12217721Iodo benzene diacetateHCID 672297076-Fluoro-2-((2-(pyridin-2-yl)hydrazono)methyl)-8-(triisopropylsilyloxy)quinoline

Produkt 1

HCID 672334852-([1,2,4]Triazolo[4,3-a]pyridin-3-yl)-6-fluoro-8-(triisopropylsilyloxy)quinolineAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

6-Fluoro-2-((2-(pyridin-2-yl)hydrazono)methyl)-8-(triisopropylsilyloxy)quinoline (10 g, 23 mmol) was weighed into a 1000 mL 1 neck round bottom flask, followed by addition of iodo benzene diacetate (8.1 g, 25 mmol) and 400 mL of dichloromethane. The mixture was stirred at ambient temperature for 24 hours, at which time the reaction was complete. The crude mixture was partitioned with Na2S2O3, back extracted with DCM, and the combined organics were washed with brine and dried over sodium sulfate, then concentrated in vacuo. The crude product was the purified by flash column chromatography (SP1 Biotage Horizon, 1-15% MeOH/DCM gradient elution), affording the desired product (9.4 g, 94% yield) as a white powder.

Aufarbeitung

  1. customThe crude mixture was partitioned with Na2S2O3
  2. extractionback extracted with DCM
  3. washthe combined organics were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. custompurified by flash column chromatography (SP1 Biotage Horizon, 1-15% MeOH/DCM gradient elution)

Quellen und Nachweise

ORD-Eintrag
ord-fd829a1f1ff1484e9827ccf90d10f8b3
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987251B2

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