Diisopropylethylamine → 1H-Pyrrolo[2,3-b]pyridine, 6-bromo-1-[tris(1-methylethyl)silyl]-

HRID 250689Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 250689
[Br:1][C:2]1[N:7]=[C:6]2[NH:8][CH:9]=[CH:10][C:5]2=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[Si:20](OS(C(F)(F)F)(=O)=O)([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22]>O1CCOCC1.C(OCC)(=O)C>[Br:1][C:2]1[N:7]=[C:6]2[N:8]([Si:20]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])[CH:9]=[CH:10][C:5]2=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 2724529Triisopropylsilyl trifluoromethanesulfonateHCID 111599156-Bromo-7-azaindole

Produkt 1

HCID 580876901H-Pyrrolo[2,3-b]pyridine, 6-bromo-1-[tris(1-methylethyl)silyl]-

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

6-bromo-1H-pyrrolo[2,3-b]pyridine (587, 275 mg, 1.39 mmol) was dissolved in 4 mL of dry dioxane. DIEA (3 equiv) and TIPS-OTf (2.5 equiv) were added and the reaction was stirred at 50° C. overnight. The reaction was then diluted with 20 mL of ethyl acetate and washed 2 times with 10 mL NaHCO3 (aq., 5%) and once with 10 mL brine. The organic fraction was dried over MgSO4, evaporated and diluted with 5.5 mL of dry toluene (˜10 mg bromide per 0.2 mL of solution) to use directly in the next reaction step.

Aufarbeitung

  1. washwashed 2 times with 10 mL NaHCO3 (aq., 5%)
  2. dry with materialThe organic fraction was dried over MgSO4
  3. customevaporated
  4. additiondiluted with 5.5 mL of dry toluene (˜10 mg bromide per 0.2 mL of solution)
  5. customto use directly in the next reaction step

Quellen und Nachweise

ORD-Eintrag
ord-3d66a2b0c7184c9cb8584b662d96a36f
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863288B2

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