Diisopropylamine → HCID 69221149, Verbindung

HRID 1392231Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1392231
[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[CH:13]=[CH:12][C:11](I)=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:16]([N:20]1[CH:24]=[CH:23][N:22]=[N:21]1)[CH2:17][C:18]#[CH:19].C(NC(C)C)(C)C.C(OCC)(=O)C>C1COCC1.[Cu](I)I>[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:19]#[C:18][CH2:17][CH2:16][N:20]2[CH:24]=[CH:23][N:22]=[N:21]2)=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 7912DiisopropylamineHCID 8857Ethyl AcetateHCID 17750156tert-Butyl (5-iodopyridin-2-yl)carbamateHCID 184535221-But-3-ynyl-1H-[1,2,3]triazole

Produkt 1

HCID 69221149HCID 69221149, VerbindungAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

(5-Iodo-pyridin-2-yl)-carbamic acid tert-butyl ester (3.45 g, 10.77 mmol) was dissolved in anhydrous THF (30 ml) under an argon atmosphere and treated with (PPh3)2Pd(II)Cl2 (0.6 g, 0.86 mmol) and copper iodide (0.2 g, 1.1 mmol). To this mixture a solution of 1-but-3-inyl-1H-[1,2,3]triazole (2.1 g, 17.24 mmol) in anhydrous THF (20 ml) is added dropwise at 0° C. followed by diisopropyl-amine (7.6 mL, 53.88 mmol). After stirring for 6 h at room temperature ethyl acetate (100 mL) was added, the mixture was washed with water, brine and dried over sodium sulfate. After removal of the solvents the crude product was purified by column chromatography on silica gel (dichloro methane/methanol 98:2) yielding [5-(4-[1,2,3]triazol-1-yl-but-1-ynyl)-pyridin-2-yl]-carbamic acid tert-butyl ester as light yellow solid (2.35 g, 70%).

Aufarbeitung

  1. additionwas added
  2. washthe mixture was washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. customAfter removal of the solvents the crude product
  5. customwas purified by column chromatography on silica gel (dichloro methane/methanol 98:2)

Quellen und Nachweise

ORD-Eintrag
ord-39702e1e515b4bdf902419d6b935d1b0
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07342030B2

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