8-(1-Ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine → 8-(1-Ethyl-propyl)-2,6-dimethyl-3-(2-methyl-thieno[2,3-b]pyridin-3-yl)-imidazo[1,2-b]pyridazine

HRID 226071

Reaktionsgleichung

Br[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[S:4][C:3]=1[CH3:11].[CH2:12]([CH:14]([C:17]1[C:18]2[N:19]([C:24](I)=[C:25]([CH3:27])[N:26]=2)[N:20]=[C:21]([CH3:23])[CH:22]=1)[CH2:15][CH3:16])[CH3:13]>C1COCC1.[Zn]>[CH2:12]([CH:14]([C:17]1[C:18]2[N:19]([C:24]([C:2]3[C:10]4[C:5](=[N:6][CH:7]=[CH:8][CH:9]=4)[S:4][C:3]=3[CH3:11])=[C:25]([CH3:27])[N:26]=2)[N:20]=[C:21]([CH3:23])[CH:22]=1)[CH2:15][CH3:16])[CH3:13]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

382 mg of 3-Bromo-2-methyl-thieno[2,3-b]pyridine (1.67 mmol) is placed into the vial with 2.5 ml of Reiki Zn, suspension in THF (1.75 mmol) and capped and heated at 100° C. for 2 h. The excess Zinc is allowed to settle down and the solution is transferred to the vial containing 200 mg of 8-(1-ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.58 mmol) and 41 mg of PdCl2(pddf) (0.05 mmol) in 3 ml of dry THF. The vial is capped with a Teflon cap and heated at 80° C. for 2 days. The reaction mixture is quenched with sat. NH4Cl and extracted by CH2Cl2, dried over Na2SO4 and evaporated. The crude product is applied onto a silica-gel chromatography column (Hexane:AcOEt=8:1) to give 22 mg of the title compound. Yield 4%. mass spectrum (m/e): 365 (M+1).

Aufarbeitung

customcapped
customcap
temperatureheated at 80° C. for 2 days
customThe reaction mixture is quenched with sat. NH4Cl
extractionextracted by CH2Cl2
dry with materialdried over Na2SO4
customevaporated

Quellen und Nachweise

ORD-Eintrag: ord-18e3f1ab9d99438a991b30b2471e11d5
Quelldatensatz: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07557103B2

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