Imidazole → 4-(2-Triisopropylsilanyloxy-ethylamino)-nicotinonitrile

HRID 2264914Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2264914
[OH:1][CH2:2][CH2:3][NH:4][C:5]1[C:10]([C:11]#[N:12])=[CH:9][N:8]=[CH:7][CH:6]=1.N1C=CN=C1.[CH:18]([Si:21](Cl)([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:24])[CH3:23])([CH3:20])[CH3:19]>CN(C=O)C>[CH:18]([Si:21]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[O:1][CH2:2][CH2:3][NH:4][C:5]1[C:10]([C:11]#[N:12])=[CH:9][N:8]=[CH:7][CH:6]=1)([CH3:20])[CH3:19]

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 59596532HCID 59596532, Verbindung

Produkt 1

HCID 595964584-(2-Triisopropylsilanyloxy-ethylamino)-nicotinonitrileAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 4-(2-hydroxy-ethylamino)-nicotinonitrile (500 mg, 3.07 mmol) and imidazole (250 mg, 3.68 mmol) in DMF (15 mL) was added triisopropylsilyl chloride (0.723 mL, 3.37 mmol). The reaction mixture stirred at room temperature for 2 hours. The mixture was then partitioned between ethyl acetate and water, the organic layer isolated and washed with brine, dried (Na2SO4), filtered and concentrated. The resultant residue was purified by flash chromatography (Si-PPC, pentane:ether, gradient 50:50 to 30:70) to provide the title compound as a white solid (753 mg, 77%). LCMS (method B): RT=2.92 min, M+H+=320.

Aufarbeitung

  1. customThe mixture was then partitioned between ethyl acetate and water
  2. customthe organic layer isolated
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resultant residue was purified by flash chromatography (Si-PPC, pentane:ether, gradient 50:50 to 30:70)

Quellen und Nachweise

ORD-Eintrag
ord-bb9d240a7c964ce4a65cce478075a9e2
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07855216B2

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