N-Iodosuccinimide → HCID 68839933, Verbindung

HRID 1432657Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1432657
[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:17]3[S:18][CH:19]=[CH:20][C:21]=3[O:22][CH3:23])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2].C1C(=O)N([I:31])C(=O)C1>CC#N>[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:17]3[S:18][C:19]([I:31])=[CH:20][C:21]=3[O:22][CH3:23])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2]

Komponenten

4

Edukt 2

HCID 120273N-IodosuccinimideHCID 57932986HCID 57932986, Verbindung

Produkt 1

HCID 68839933HCID 68839933, VerbindungAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 8-(1-ethyl-propyl)-3-(3-methoxy-thiophen-2-yl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.75 g, 2.28 mmol) and CH3CN (10 mL) is added NIS (0.54 g, 2.39 mmol). The solution is stirred overnight, concentrated, diluted with EtOAc (30 mL), washed with water (30 mL), sat. NH4Cl (30 mL), 20% (NaHSO3) (30 mL), brine (30 mL), dried over MgSO4, filtered and concentrated. The residue is purified by ISCO column chromatography (15%-20% EtOAc/hexane gradient) furnish the title compound (0.91 g, 2.00 mmol, 88%). 1H NMR (CDCl3) δ 0.85 (t, J=7.5 Hz, 6H), 1.71-1.89 (m, 4H), 2.46 (s, 3H), 2.52 (s, 3H), 3.25-3.35 (m, 1H), 3.83 (s, 3H), 6.64 (s, 1H), 7.12 (s, 1H). LC/MS (m/z): calcd. for C18H22IN3OS (M+H)+: 456.4; found: 456.0.

Aufarbeitung

  1. concentrationconcentrated
  2. additiondiluted with EtOAc (30 mL)
  3. washwashed with water (30 mL), sat. NH4Cl (30 mL), 20% (NaHSO3) (30 mL), brine (30 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified by ISCO column chromatography (15%-20% EtOAc/hexane gradient)

Quellen und Nachweise

ORD-Eintrag
ord-70cd8e4ded6b45729caca18bc5a46bb0
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612067B2

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