N-Iodosuccinimide → 8-(1-Ethyl-propyl)-3-iodo-2-methyl-6-trifluoromethyl-imidazo[1,2-b]pyridazine

HRID 226030Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 226030
[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([CH:16]=[C:17]([CH3:19])[N:18]=2)[N:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[CH2:4][CH3:5])[CH3:2].C1C(=O)N([I:27])C(=O)C1>CC#N.CCOC(C)=O>[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:16]([I:27])=[C:17]([CH3:19])[N:18]=2)[N:9]=[C:10]([C:12]([F:13])([F:15])[F:14])[CH:11]=1)[CH2:4][CH3:5])[CH3:2]

Komponenten

5

Edukt 2

HCID 120273N-IodosuccinimideHCID 688564838-(1-Ethyl-propyl)-2-methyl-6-trifluoromethyl-imidazo[1,2-b]pyridazine

Produkt 1

HCID 688564568-(1-Ethyl-propyl)-3-iodo-2-methyl-6-trifluoromethyl-imidazo[1,2-b]pyridazineAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 8-(1-ethyl-propyl)-2-methyl-6-trifluoromethyl-imidazo[1,2-b]pyridazine (0.18 g, 0.67 mmol) in CH3CN (5 mL) is treated with NIS (0.18 g, 0.80 mmol), and stirred at rt overnight. It is diluted with EtOAc (50 mL), washed with 5% Na2SO3 (2×25 mL); dried (Na2SO4), filtered and concentrated to give the title compound (0.26 g, 0.65 mmol, 98%). 1H NMR (CDCl3): δ 0.85 (t, J=7.0 Hz, 6H), 1.79-1.92 (m, 4H), 2.59 (s, 3H), 3.30-3.43 (m, 1H), 7.09 (s, 1H). ES-MS (m/z): calcd for C13H15F31N3 (M+H)+: 398.2. found: 398.1.

Aufarbeitung

  1. washwashed with 5% Na2SO3 (2×25 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-9c29c5a295354a5c9d049a49934ccd07
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557103B2

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