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

HRID 226081

Reaktionsgleichung

[Br: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.[CH2:16]([CH:18]([C:21]1[C:22]2[N:23]([C:28](I)=[C:29]([CH3:31])[N:30]=2)[N:24]=[C:25]([CH3:27])[CH:26]=1)[CH2:19][CH3:20])[CH3:17]>C1COCC1.CCCCCC.[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]>[Br:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[S:4][C:3]=1[C:28]1[N:23]2[N:24]=[C:25]([CH3:27])[CH:26]=[C:21]([CH:18]([CH2:16][CH3:17])[CH2:19][CH3:20])[C:22]2=[N:30][C:29]=1[CH3:31]

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

214 mg of 3-Bromo-thieno[2,3-b]pyridine (1.0 mmol) is dissolved in 1.5 ml of dry THF and cooled to −78° C. 0.44 ml of n-butyl lithium 2.5M in hexane is added slowly and stirred at −78° C. for 10 min. 2.2 ml of 0.5 M ZnCl2 in THF (1.1 mmol) is added and stirred at room temperature for 20 min. 274 mg of 8-(1-ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.8 mmol) and 33 mg of PdCl2(dppf) (0.04 mmol) are added. The reaction vial is capped and heated at 80° C. for 3 days. The reaction is filtered and applied onto a silica-gel chromatography column (Hexane: AcOEt=8:1) to give 49 mg of the 3-(3-bromo-thieno[2,3-b]pyridin-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (11%) and 33 mg of reduced compound, 8-(1-ethyl-propyl)-2,6-dimethyl-3-thieno[2,3-b]pyridin-2-yl-imidazo[1,2-b]pyridazine, (9%).

Aufarbeitung

stirringstirred at room temperature for 20 min
customThe reaction
customvial is capped
temperatureheated at 80° C. for 3 days
filtrationThe reaction is filtered

Quellen und Nachweise

ORD-Eintrag: ord-426f934548c54c0f838e276d03bef3fe
Quelldatensatz: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07557103B2

Verknüpfte Notizen

Wird geladen…