3-(4,5-Dibromo-3-methyl-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine → 3-(4-Bromo-3-methyl-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine

HRID 1432612Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1432612
[Br:1][C:2]1[C:3]([CH3:24])=[C:4]([C:8]2[N:12]3[N:13]=[C:14]([CH3:22])[CH:15]=[C:16]([CH:17]([CH2:20][CH3:21])[CH2:18][CH3:19])[C:11]3=[N:10][C:9]=2[CH3:23])[S:5][C:6]=1Br.[Li]CCCC>C1COCC1>[Br:1][C:2]1[C:3]([CH3:24])=[C:4]([C:8]2[N:12]3[N:13]=[C:14]([CH3:22])[CH:15]=[C:16]([CH:17]([CH2:20][CH3:21])[CH2:18][CH3:19])[C:11]3=[N:10][C:9]=2[CH3:23])[S:5][CH:6]=1

Komponenten

4

Edukt 2

HCID 579330673-(4,5-Dibromo-3-methyl-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazineHCID 178418339Butyllithium

Produkt 1

HCID 579329703-(4-Bromo-3-methyl-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazineAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a −78° C. solution of 3-(4,5-dibromo-3-methyl-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.22 g, 0.47 mmol) and THF (3 mL) is added 1.6 M n-BuLi (0.31 mL, 0.49 mmol). After 20 minutes the solution is quenched with water (1 mL), warmed to ambient temperature, diluted with EtOAc (30 mL), washed with brine (30 mL), dried over MgSO4, filtered and concentrated. The residue is purified by ISCO (5%-10% EtOAc gradient) furnish the title compound (0.056 g, 0.14 mmol, 31%). 1H NMR (CDCl3) δ 0.87 (t, J=7.5 Hz, 6H), 1.73-1.93 (m, 4H), 2.09 (s, 3H), 2.44 (s, 3H), 2.49 (s, 3H), 3.27-3.36 (m, 1H), 6.68 (s, 1H), 7.44 (s, 1H). LC/MS (m/z): calcd. for C18H22BrN3S (M+H)+: 392.2; found: 392.3.

Aufarbeitung

  1. customAfter 20 minutes the solution is quenched with water (1 mL)
  2. additiondiluted with EtOAc (30 mL)
  3. washwashed with brine (30 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified by ISCO (5%-10% EtOAc gradient)

Quellen und Nachweise

ORD-Eintrag
ord-5b49310781f24e329a2b78a9fed3a642
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612067B2

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