Hexane → 3-(3-Chloro-thieno[2,3-b]pyridin-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine

HRID 226083

Reaktionsgleichung

Reaktionsgleichung von HRID 226083
[Cl:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[S:4][CH:3]=1.C([Li])CCC.CCCCCC.[CH2:22]([CH:24]([C:27]1[C:28]2[N:29]([C:34](I)=[C:35]([CH3:37])[N:36]=2)[N:30]=[C:31]([CH3:33])[CH:32]=1)[CH2:25][CH3:26])[CH3:23]>C1COCC1.[Cl-].[Cl-].[Zn+2].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[S:4][C:3]=1[C:34]1[N:29]2[N:30]=[C:31]([CH3:33])[CH:32]=[C:27]([CH:24]([CH2:22][CH3:23])[CH2:25][CH3:26])[C:28]2=[N:36][C:35]=1[CH3:37]

Komponenten

8

Edukt 4

HCID 8058HexaneHCID 5981913-Chlorothieno(2,3-b)pyridineHCID 577526818-(1-Ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazineHCID 178418339Butyllithium

Produkt 1

HCID 577526133-(3-Chloro-thieno[2,3-b]pyridin-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3007855ZincchlorideKatalysatorHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

250 mg of 3-Chloro-thieno[2,3-b]pyridine (1.5 mmol) is dissolved in 2.0 ml of dry THF and cooled to −78° C. 0.59 ml of n-butyl lithium 2.5 M in hexane (1.5 mmol) is added slowly and stirred at room temperature for 3 min and cooled to −78° C. 3.0 ml of 0.5 M ZnCl2 in THF (1.5 mmol) is added and stirred at room temperature for 20 min. 343 mg of 8-(1-ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine (1.0 mmol) and 41 mg of PdCl2(dppf) (0.05 mmol) are added and the reaction vial is capped with a Teflon cap and heated at 80° C. overnight. The reaction mixture is concentrated and applied onto a chromatography silica-gel column (Hexane:AcOEt=3:1); mass spectrum (m/e): 385; 1H-NMR (CDCl3): 8.66 (dd, 1H, J=4.5 Hz, 1.5 Hz), 8.10 (dd, 1H, J=8.1 Hz, 1.5 Hz), 7.44 (1H, J=8.1 Hz, 4.5 Hz), 6.74 (s, 1H), 3.33 (m, 1H), 2.55 (s, 3H), 2.53 (s, 3H), 1.85 (m, 4H), 0.89 (t, 6H, J=7.5 Hz) ppm.

Aufarbeitung

  1. temperaturecooled to −78° C
  2. stirringstirred at room temperature for 20 min
  3. customthe reaction
  4. customcap
  5. temperatureheated at 80° C. overnight
  6. concentrationThe reaction mixture is concentrated

Quellen und Nachweise

ORD-Eintrag
ord-77a5ccbc089b4af9a27ad748123c229e
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557103B2

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